• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
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    • 专利摘要:
    A racemic or optically active alkyl 2-chloropropionate is prepared, respectively, from a racemic or optically active alkyl lactate by, in a first step, gradually bringing the alkyl lactate into contact with the thionyl chloride, in the presence of an organic base, while maintaining, in the reaction mixture, an excess of thionyl chloride, relative to the amount of alkyl lactate introduced into this mixture, at a temperature below the decomposition point of the chlorosulphinate of the alkyl lactate, which is formed as an intermediate, and then, in a second step, in heating the reaction mixture resulting from the first step at a temperature which is at least equal to the decomposition point of the chlorosulphinate of the alkyl lactate. The alkyl 2-chloropropionates can be used for the manufacture of the racemic or optically active 2-phenoxypropionic acids.
    公开号:SU1266468A3
    申请号:SU802933751
    申请日:1980-06-17
    公开日:1986-10-23
    发明作者:Бюатье Бернар；Бернар Андре
    申请人:Рон-Пуленк Агрошими (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to an improved method for producing optically active L-2-chloromethylpropionate, which is used as a starting compound in the preparation of D-2-phenoxypropionic acids.
    The aim of the invention is to increase the optical purity of the product due to the interaction of D-methyl lactate with thionyl chloride by introducing these reagents in the reaction zone in batches, and maintaining the reaction mixture of an excess of thionic Chloride in an amount of 7.5-12 mol% with respect to D-methyl lactate in the presence of an organic base such as pyridine or quinoline, in an amount of 0.12-0.83% by weight of D-methyl lactate at 60- 80 C, followed by heating the resulting reaction mixture to 75-80 ° C until gas evolution ceases.
    PRI me R 1. Use a flask equipped with a stirrer, a Vigreux type refrigerator, a thermometer, a funnel 'for introducing products and collection funnels with liquid nitrogen located behind the refrigerator.
    832 g (8 mol) of D-methyl lactate [oij p ° = +7.48 (without solvent) are placed in a funnel for introducing the product, a. 1060 g (8.9 mol) of thionyl chloride and 4.15 g of pyridine (0.49 wt.% of the amount of converted methyl lactate) are placed in the flask.
    Methyl lactate contains "as: impurities about 1.03% ethyl lactate and 0.61% other impurities, including methyl lactyl lactate.
    The temperature in the flask was brought to 60 ° C with stirring, after which methyl lactate was introduced for 4 hours, maintaining the indicated temperature at a constant level. After the introduction of the product, the temperature in the flask was adjusted to 75 ° C and maintained for 1 hour. Chromatographic analysis of the gas phase carried out at this moment showed that the reaction mixture no longer contained methyl lactate. The reaction mixture is heated for another 20 minutes, after which it is cooled for 20 minutes under a vacuum of 150 mm Hg. up to 40-45 C.
    992.5 g (884 ml) of crude product is obtained containing crude 2-chloromethylpropionate, S0 2 (19.2 g), SOC1 4 (1.6 g) and HC1 (1.8 g)
    Chromatographic gas analysishowl phase obtained untreated 5 2-chloromethylpropionate shows the nextblowing composition, wt.% (except SO,,SOClj, HC1 and pyridine): 2-chloromethylpropionate 97.7Ethylchlorpropion. T1.22 10 Methylacetylactate Methylacetylactyl-0.04lactate0.08Methyl Lactate Chloro- propionate0.67 fifteen 'Ethyl lactate-chloro- propionate0.01Lactide (cyclic methyl lactate) Methyl'ctyl lactate -0,03 20 Chlorpropionate Unidentified0, 11impurities0.14 '• Formation of ethyl chloropropionate,methylacetylactate and methylacetyl-
    lactyl lactate is the result of impurities contained in the starting methyl lactate.
    The yield of 2-chloromethylpropionate is 98%.
    900 g of the obtained crude product are distilled at a pressure of 20 mm Hg. in a packed column 40 cm high. At the end of the distillation, the vacuum is increased to 3 mmHg. At the outlet of the packed column 5 neskon3 condensed vapors enter the trap with liquid nitrogen.
    Distillation makes it possible to obtain the following three fractions: 95 g of 2-chloromethylpropionate with a rotational capacity of 40 j j '= - 25.37 ° (without solvent); 675 g of 2-chloromethylpropionate with a rotational ability of foe] 5 = - 25.26 ° (without solvent) and 71 g of 2-chloromethylpropionate with a rotational capacity of 45 ° p ~ ~ 24.56 ° (without solvent),
    13 g of the residue formed by heavy ao compounds are recovered from the bottom of the column.
    17 g of 2-chloromethylpropionate containing traces of HC 1, S0 2 and SOC1 2 are recovered from a liquid nitrogen trap.
    The yield after distillation, taking into account the 1st recovered 2-chloropropionate in a trap with nitrogen, is 97.2%.
    L-2-chloromethylpropionate has a rotational capacity of ~ ~ 27.8 (without solvent). With this indicator in mind, the optical purity of 2-chloropropionate obtained as a result of the second 5 distillation fraction is 95.41 (i.e., the obtained compound consists of 95.4% of isomer L and 4.6% of isomer D).
    . D-methyl lactate has a rotational ability (X] ^ = + 8.2 (without solvent). With this indicator in mind, the optical purity of the starting methyl lactate is 95.6%. Thus, 'the conversion of methyl lactate to 2- * 5
    methylpropionate does not entail significant racemization.
    Example!. The experiment is carried out under conditions analogous to example 1, using, at the same time, gj methyl lactate 20 having the rotational ability indicated in example 1, 832 (8 mol); thionyl chloride 1070 (8.99 mol) and pyridine 2.1.
    Introduction methyl lactate osuschestvlya- dissolved PRTS 2 ^ 60 ° C for 4h, then are heated to 75 ° C for 1 h 30 min.
    After cooling at partial vacuum remove 906, 5 ml (1020 g) thirty crude product containingcrude 2-chloromethylpropionate,S0 5 (42.9 g), SOC1 2 (14 (0 * 75 g). , 42 g) INS1Chromatographic gas analysis 35 howl phase obtained crude 2-chloromethylpr opionate showsnext composition, may. %:.2-chloromethylpropionate 97.49 "Ethyl Chloropropionate 1.26 40 Methylacetylactate 0.04Methylacetillac -tillactate 0.09Methyl Lactate Chloro- ' propionate 0.80 45 Ethnlactate Chloropropionate Lactide (cyclic 0.01sky methyl lactate) Yetillactyl 0.04 fifty Tatchlorpropionate Unidentified 0.14impurities 0.13Distillation of 900 g of crude
    2-chloromethylpropionate allows-; 55 radiate the following fractions: head 98 g 3 - 25.10 ° (without solvent); central - 663 T W = - 25.36 ° (without solvent); tail - 55 g ~ 25.00 ° (without 'solvent).
    8.5 g of the residue formed by heavy products are collected at the bottom of the column.
    37 g of 2-chloromethylpropionate containing traces of HC1, S0 2 and SOCl is collected in a liquid nitrogen trap. ”After the distillation of the methyl methylpropionate, taking into account the product recovered in a trap with nitrogen, it is 98.6%. · Optical purity calculated on the central fractions , 95.6%.
    Example Z. The experiment is carried out under conditions similar to example 1, using at the same time, g: · methyl lactate having rotational ability,. 1.832 (8 mol) indicated in example; ^ thionyl chloride 1070 (8.99 mol) and pyridine 1.
    “The introduction of methyl lactate is carried out at 60 ° C for 4 hours, followed by heating to 75 ° C for 2 hours
    - After cooling under partial vacuum, 1026 g (910 ml) of a crude product containing crude 2-chloromethyl propionate is obtained,
    SO, (42.5 g) and SOC1 2 (22.8 g). In a liquid nitrogen trap 44.5 ml (70 g) are collected 2-chloromethyl- propionate containing , g: SO, 11.3, JS1 12.9 (291.67 g / l) and thionyl chloride 40.0.Chromatographic analysis of gas phase of the obtained crude 2-chloro- methylpropionate shows the following composition, wt.%:2-chloromethyl propionate 97.53 Ethyl Chloropropionate 1.15 Methylacetylactate 0.04 . Methylacetylactyl-lactate 0.08 Methyl Lactate Chloro-propionate 0.67. Ethyl lactate chloropropionate 0.01 Lactide (cyclicmethyl lactate) 0.04 Methyl lactyl lactatechlorpropionate 0.34 Unidentifiedimpurities 0.14
    Distillation of 900 g of non-obtained. purified methylchloropropionate allows to obtain the following fractions:
    1266468 6 head - 99 g = - 25.29 e (without solvent); central - 652 g [“G p =” 25.34 (without solvent); tail - 58 g = - 24.97 ° (without solvent). 5
    9 g of the residue formed by heavy products are collected at the base of the column.
    In a liquid nitrogen trap,, 0 , 29 g of 2-chloromethylpropionate are collected.
    The yield after distillation of 2-chloromethylpropionate, taking into account the product recovered from the traps, is 98.2%.
    Optical Purity of 2-chloromethylpropionate obtained after distillation (central fraction) 95.5%.
    Example 4. In a flask equipped with a stirrer, a Vig- 20 re-type refrigerator and two funnels for introducing the initial product, g: thionyl chloride 50 (0.42 mol) is charged; pyridine 4.15 and 2-chloromethylpropionate, previously prepared, with a rotational capacity of {Xlif and ~ 24.8 ° (without solvent) 500.
    832 g (3 mol) of methyl lactate хГ = + 7.48 ° (without solvent), containing 1.03% ethyl lactate and 0.61% of other unidentified impurities in the form of impurities, are measured in one of the funnels for product introduction. 973 g (8.18 mol) of thionylchloro-35 Reed are placed in another funnel for product introduction.
    At the same time, methyl lactate and tisnyl chloride are introduced into the flask for 4 hours at 60 ° С, regulating the amount of introduced reagents in such a way that the amount of thionyl chloride introduced into the flask is always in molar excess of at least 2.5% with respect to the amount of introduced methyl lactate . 45
    After the introduction of the above reagents is completed, the temperature of the reaction mixture is raised from 60 to 75 ° C in 5 minutes and this temperature is maintained for 1 hour 30 minutes Obtain 1588 g of 50 crude * L product consisting of more than 90% methyl chloropropionate.
    By distillation, 1588 g of the obtained crude product, carried out in a packed column 40 cm high with a partial vacuum of 48 mm ^ t., Brought at the end of the distillation;
    qing up to 3 mm Hg, three fractions are distinguished:
    The first fraction (263 g) was formed, g: 2-chloromethylpropinate, containing about 1 wt.% 2-chlorosyl propionate, 247.5; thionyl chloride 13.1; free S0 2 1.3 and free HC1 1.0.
    . The second fraction (1035.4 g) [<l] ^ ~ = - 25.06 ° (without solvent) was formed ^: a mixture of 2-chloromethyl propionate and 2-chloroethyl propionate containing about 1 wt.% 2-chloroethyl propionate, 1033.6% ; S0 0.9 and NA '0.9.
    The third fraction (129 g) ~ I - 24.58 ° (without solvent), g: 2-chloromethylpropionate containing about 1 wt.% 2-chloroethylpropionate, 128.9 and HC 1 0.07.
    From the base of the column, g of the residue formed by pyridine hydrochloride and heavy products is recovered.
    After distillation, washing the colonies allows the recovery of 6 g of 2-chloromethylyropionate.
    The yield of 2-chloromethylpropionate is 94%.
    Example 5. In a container with a volume of l equipped with a stirrer, a refrigerator and two dropping funnels, 150 g of thionyl chloride (1.26 mol) and 3.2 g of quinoline are charged.
    1040 g (10 mol) of methyl lactate W® = + 7.83 (optical purity * 97.8%) is fed into one dropping funnel and 1129 g of thionyl chloride to the other.
    At the same time, the contents of both funnels enter the container for 4 hours from two dropping funnels, while maintaining a temperature of 59 - 62 ° С. ''
    At the end of the introduction, the temperature is raised to 75 ° C and this temperature is maintained until the end of gas targeting. 1334 g of crude material are obtained.
    By distillation, 502 g of the crude material are first separated first fraction (105 g), then the second fraction (309 g), ("g,] ® I - 26.15 ° (optical purity 97%), the residue is 8 g.
    Example Use a device similar to that specified in example 1.
    1248 g (12 mol) of methyl lactate = + 7.9 ° (without solvent) are placed in a dropping funnel, and 1572 g (13.2 mol) of thionyl chloride and 2 L of 6 g (0.033 mol) of pyridine (in mass
    0.20% of the amount of converted lactate).
    Set the temperature in the container to 80 ° C and introduce methyl lactate for 3 hours, keeping this temperature 5 at a constant level. · At the end of the introduction, maintain the temperature at 80 ° C for another 1 hour and 15 minutes.
    The resulting product is distilled in a packing column having a height of 10 70 cm, under a vacuum of 20 mm Hg. and get 2-chloromethylpropionate with optical activity.
    Yield 96.6%, Rotational ability 15 = - 25.9 ° (without solvent).
    The optical purity of the starting methyl lactate is 98.1%. The optical purity of the obtained 2-chloromethylpropionate 96.6%. 20
    权利要求:
    Claims (3)
    [1]
    The invention relates to an improved process for the preparation of an optically active L-2-chloromethyl propionate, which is used as a starting compound in the preparation of D-2-phenoxy-propionic acids. The aim of the invention is to increase the optical purity of the product due to the interaction of P methyl lactate with thionyl chloride by introducing these reagents into the reaction zone in batches, and maintaining an excess of thionyl chloride in the reaction mixture in the amount of 7.5–12% mol. with respect to B-methyl lactate in the presence of an organic base, such as pyriDip or quinoline, in an amount of 0.12-0.83% by weight of D-methyl lactate at 60-80 ° C, followed by heating the resulting reaction mixture to 75-80 ° C to termination of gas evolution. EXAMPLE 1 A flask equipped with a stirrer, 5; a Vigree type freezer, a thermometer, a funnel for the introduction of products and a funnel for trapping with liquid nitrogen located behind the cooler, is used. 832 g (8 mol) of D-methyl lactate oi} p °, 48 (without solvent) are placed in a funnel for the introduction of the product. 1060 g (8.9 mol of thionyl chloride and 4.15 g of pyridine (0.49 wt.% of the amount of methyl lactate to be converted) are placed in a flask. Methyl lactate contains about 1.03% ethyl lactate and 0.61% of other impurities as impurities, among them methyl lactyl lactate, the temperature in the flask is brought to 60 ° C with stirring, after which methyl lactate is introduced for 4 hours, maintaining the indicated temperature at a constant level. After the introduction of the product is completed, the temperature in the flask is brought to 75 ° C and maintain e for 1 h. Chromatographic analysis of the gas phase carried out in this the moment indicates that methyl lactate is no longer contained in the reaction mixture, and the mixture is heated for another 20 minutes, after which it is cooled for 20 minutes under a vacuum of 150 mm Hg to 40-45 ° C. , 5 g (884 ml) of an uncleaned product containing unpurified 2-chloromethylpropionate SO (19.2 g), 8001 (1.6 g) and HC1 (1.8 g). The chromatographic analysis of the gas phase of the resulting crude chloromethylpropionate shows the following composition. , wt.% (except 80, OClj, HCl and pyridine): 2-chloromethyl propionate 97.7 Ethyl chloropropionate 1.22 Methyl acetate shaktat 0.04 Me methylacyl lactate lactate, 08 Methyl lactate chloropropionate, 67 Ethyl lactate chloropropionate, 0.01 Lactide (cyclic methyl lactate) 0.03 Methyllactyllactic.thichloropropionate 0.11 Unspecified impurities 0.14 Formation of ethyl chloropropionate, ethyl acetate and lactic methylcityltelectylacrylate, etc. The yield of 2-chloromethylpropionate 98%. 900 g of the obtained crude product is distilled at a pressure of 20 mm Hg, in a 40 cm high pressure column. At the end of the distillation, the Akum grows to 3 mm Hg. At the exit of the packed column, non-condensed vapors enter the catcher with liquid nitrogen. Distillation allows to obtain the following tr) and fractions; 95 g of 2-chloromethylproperipate with a torque of ctj and ° - 25.37 ° (without solvent); 675 g of 2-chloromethyl propionate with a rotating capacity of Mj, -25.26 (without solvent) and 71 g of 2-chloromethylpropionate with a rotating capacity of OZ p ° -24.56 (without solvent). From the bottom of the column, 13 g of the residue yellow compounds of m1-1. 17 g of 2-chloromethyl propionate containing traces of HC1, S02 and SOClj are recovered from the liquid nitrogen trap. The yield after distillation, taking into account the recovered 2-chloropropionate in the trap, is 97.2%. L-2-chloromethyl propionate has a dispensing capacity of about 27.8 (without solvent). In view of this, the optical purity of the 2-chloropropionate obtained in the resultant second distillation fraction is 95.41 (i.e., the resulting compound consists of 95.4Z isomers L and 4, b (isomer D). D -methyl lactate has a rotational ability of 8.2 (without solvent). Taking this indicator into account, the optical purity of the initial methyl scattate is 95.6 Z. Thus, the transition of methyl lactate to 2-methyl propionate does not entail significant racemization. And p and m e p 2. The experiment was carried out under conditions analogous to example 1, using, however, g; t, having the rotational ability indicated in example 1, 832 (8 mol) thionyl chloride 1070 (8.99 ml) and pyridine 2.1. Introduction of methyl lactate was carried out for 4 h, after which heating was carried out to 75 ° C for 1 h 30 minutes After cooling under partial vacuum, 906.5 ml (1020 g) of crude product containing crude 2-chloromethyl propionate, S0j (42.9 g), SOC1 .. (14.42 g) and HC1 (g) are recovered. Chromatographic analysis of the gaseous phase of the obtained crude 2-chloromesh1 propionate shows the following composition, wt.X: 2-chloromethyl propionate 97.49 Ethyl chloropropionate 1.26 Methylace illaktat0,04 4-, Metilatsetillak-. tillactate 0.09 Methyl lactate chloropropionate, 80 Ethyl lactate chloropropionate, 01 Lactide (cyclic methyl lactate) 0.04 Yetyllactyl lactate chloropropionate 0.14 Unspecified impurities 0.13 Distillate 900 g of crude 2-chloromethylene propionate allows the following fractions to be obtained: head, head 900 g of crude 2-chloromethylene propionate allows the following fractions to be obtained: - 25.10 ° (without dissolved bodies); Central - 663 T - 25.36 (without solvent); tailings - 55 g “s - 25.00 ° (without solvent). At the bottom of the column, 8.5 g of the residue formed by heavy products are collected. 37 g of 2-chloromethylpropionate containing traces of HC1, SOj and SOClj are collected in a liquid azoTaphank. After the distillation of methyl chloropropionate, the code given for the product recovered in the nitrogen trap is 98.6%. Optical purity calculated for the central fraction, 95.6%. EXAMPLE 3: The experiment was carried out under conditions analogous to example 1 using g :, methyl lactate, having a rotational capacity,. 1.832 (8 mol) in Example; thionyl chloride 1070 (8.99 mol) and pyridine 1. Methyl lactate is introduced at 4 hours, followed by heating to 75 ° C for 2 hours. After cooling under partial vacuum, 1026 g (910 ml) of crude product containing crude 2-chloromethyl propionate, 50 (42.5 g) and SOClj (22.8 g) are obtained. 44.5 ml (70 g) of 2-chloromethyl propionate containing g: SO, 11.3, JCl 12.9 (291.67 g / l) and thionyl chloride 40.0 are collected in a liquid nitrogen trap. Chromatographic analysis of the gas phase chlorpropionate 0,34 Unidentified impurities, 14. Distilla qi 900 g of the resulting non-. purified methyl chloropropionate allows to obtain the following fractions: $ 1 goly per - 99 g 25.29 (without rastnoritep); ueiiTjiaJibHafl - 652 g C p 25.34 (without solvent); kaostova - 58 g o- ° - 24.97 ° (without solvent). At the base of the column, 9 g of residue formed from heavy products are collected. In the liquid nitrogen collector, 29 g of 2-chloromethyl propionate are collected. The yield after the distillation of the 2-chloromethyl propionate, taking into account the product recovered from the catchers, is 98.2%. The optical purity of the 2-chloromethylpropionate obtained after distillation (central fraction) was 95.5%. Example4. In a flask equipped with a stirrer, a Vigre-type cooler and two funnels for the introduction of the initial product, rs thionium chloride 50 (0.42 mol) 5 pyridine 4.15 and 2 chloromethyl propionate, previously prepared, with a rotational capacity of 24.8, are charged. ° (without solvent) 500. In one of the funnels for the introduction of the product, 832 g (3 mol) meats of lactate + 7.48 ° (without solvent) containing 1.03% ethyl lactate and 0, 61% other Unidentified Impurities. 973 g (8.18 mol) of thionyl chloride are placed in another funnel for the introduction of the products. In parallel, methyl lactate and thionyl chloride are introduced into the flask for 4 hours while regulating the amount of reagents injected so that the amount of thionyl chloride introduced into the flask is always in excess of molar at least 2.5% relative to the amount of methyl lactate introduced. After the introduction of the introduction of the reagent: reagents for 5 minutes, raise the temperature of the reaction mixture from 60 to 5 seconds and maintain this temperature for 1 hour and 30 minutes. A half of 1588 is a pure product consisting of more than 90% methyl chloropionate. By distillation of 1588 g of the obtained impure product, realized in a packed column, height 40 cm, with a partial vacuum of 48 mm jpT.CT., brought at the end of the distillate 86 in. To 3 mm Hg, there are three races: (263 g) is formed, g: 2-chloromethyl propinate, containing about 1 wt.% 2-propiate 1 propionate, 247.5; thionyl chloride 13.1; free SO 1,3 and free HC1 1,0. . The second fraction (1035.4 g) "l - 25.06 (without solvent) is formed, g is a mixture of 2-chloromethyl propionate and 2-chloroethyl propionate, containing about 1% by weight of 2-chlorostilpropionate, 1033.6; S; so, 0.9 and HC1 0.9. The third fraction (129 g) ei is 24.58 (without solvent), g: 2-chloromethyl propionate, containing about 1% by weight of 2-chloroethylpropionate, 128.9 and HC1 0.07. 14 g of residue from pyridine hydrochloride and heavy products are recovered from the base of the column. After distillation, washing the colonies allows recovery of 6 g of 2 chloromethyl pyropic. Code 2-5ShormeTilpropionat 94%. Example 5. In a container with a volume of 2 liters, equipped with a stirrer, a refrigerator and two dropping funnels, load 150 g of thionyl chloride (1.26 mol) and 3.2 g of quinoline. In one of the caps; 1040 g (10 mol) of methyl lactate S 7g83 (optical purity: 97.8%) are fed to the funnels, and 1129 g of thionyl chloride to the other. At the same time, from two dropping funnels, the reservoir contains the contents of both funnels for 4 hours and the temperature is maintained at 59–22 ° C. At the end of the intake, the temperature is raised to and maintained at this temperature until the end of the raaosbjnffeneş. 1334 g of crude material are obtained. By distillation, 502 g of the crude material is separated first by the first fraction (105 g), then atoria fraction (309 g), M is-26.15 ° (optical purity 97%), residue 8 g. Example. A device similar to the decree is used. Antagonist in nptiMere 1. A 3-drop funnel is placed 1248 g (12 mol) of methyl lactate M 7.9 ° (without solvent), and the capacity is introduced 1572 g (13.2 mol) of thioiyl chloride and 2j6 g (0.033 mol) of pyrgadine (pa weight 71 0.20% of the amount of converted lac tata). The temperature in the vessel is set and methyl lactate is introduced for 3 hours, maintaining this temperature at a constant level. After the introduction is completed, the temperature is maintained at 80 ° C for an additional 1 hour and 15 minutes. The resulting product is distilled in a packed column having a height of 70 cm, with a vacuum of 20 mm Hg. and get 2-chloromethylpropionate with optical activity. Vcode 96.6%; Rotating power - 25.9 ° (without solvent). The optical purity of the starting methyl lactate is 98.1%. The optical purity of the obtained 2-chloromethyl propionate was 96.6%. Claims 1. A method for producing optically active L-2-chloromethyl propionate by reacting thionyl chloride, in excess, with optically active D-alkyl lactate, followed by heating the reaction mixture, with In order to increase the optical purity of the product, D-methyl lactate is used as an optically active D-alkyl lactate and its interaction with thionyl chloride is carried out by introducing these reagents into the reaction zone in batches and maintaining an excess of thionyl chloride in the reaction mixture. 7.5–12 mol% relative to D-methyl lactate in the presence of an organic base, such as pyridine or quinoline, in an amount of O, 12-X), 83% by weight of D-metalactate at .b6-80 ° C, followed by heating the resulting reaction mixture to 75-80 ° C until the gassing stops.
    [2]
    2. Method POP1, characterized in that D-methyl lactate and 88.3-94.7% by weight of thionyl chloride are introduced into the reaction mixture containing the organic base and 5.3 to 11.7 wt.% Thionyl chloride.
    [3]
    3. Method POP1, characterized in that D-methyl lactate is introduced into the reaction mixture containing the organic base and thionyl chloride.
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    同族专利:
    公开号 | 公开日
    NL8003563A|1980-12-23|
    ES491618A0|1981-03-16|
    DE3023122C2|1989-09-21|
    ATA318380A|1983-10-15|
    IE49947B1|1986-01-22|
    IT1141349B|1986-10-01|
    GB2051808A|1981-01-21|
    IT8022477D0|1980-05-30|
    JPS567743A|1981-01-27|
    PL225093A1|1981-03-27|
    IL60103A|1983-07-31|
    DD151622A5|1981-10-28|
    ES8103726A1|1981-03-16|
    DK262180A|1980-12-21|
    IL60103D0|1980-07-31|
    PT71419A|1980-07-01|
    BR8003832A|1981-01-13|
    DK160935C|1991-10-21|
    GB2051808B|1983-03-02|
    JPS6366308B2|1988-12-20|
    DE3023122A1|1981-03-26|
    US4334083A|1982-06-08|
    BE883909A|1980-12-19|
    HU184790B|1984-10-29|
    DK160935B|1991-05-06|
    FR2459221A1|1981-01-09|
    LU82532A1|1982-01-20|
    FR2459221B1|1983-09-02|
    PL126964B1|1983-09-30|
    PT71419B|1981-10-22|
    AT374783B|1984-05-25|
    CA1156257A|1983-11-01|
    CH644578A5|1984-08-15|
    IE801266L|1980-12-20|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    FR1479271A|1965-12-17|1967-05-05|Rhone Poulenc Sa|New process for the preparation of optically active 2-phenoxypropionic acids|DE3102516A1|1981-01-27|1982-08-12|Hoechst Ag, 6000 Frankfurt|METHOD FOR PRODUCING OPTICALLY ACTIVE 2-CHLORINE PROPIONIC ACID ESTERS|
    GB8413155D0|1984-05-23|1984-06-27|Ici Plc|Chemical process|
    JPS6157534A|1984-08-29|1986-03-24|Daicel Chem Ind Ltd|Preparation of optically active 2-chloropropionic acid ester|
    JPS6168445A|1984-09-10|1986-04-08|Daicel Chem Ind Ltd|Continuous production of optically active 2-chloropropionic acid ester|
    JPS6226249A|1985-07-26|1987-02-04|Daicel Chem Ind Ltd|Purification of optically active lactic acid ester|
    DE3638009A1|1986-11-07|1988-05-11|Basf Ag|METHOD FOR PRODUCING 2,2-DISUBSTITUTED 3-CHLORINE PROPIONIC ACID ESTERS|
    FR2642204B1|1989-01-23|1991-04-12|Rhone Poulenc Chimie|
    EP0645365B1|1993-04-08|1997-09-10|Idemitsu Kosan Company Limited|Process for producing 2-fluoroisobutyric acid or ester thereof|
    DE19501452A1|1995-01-19|1996-07-25|Basf Ag|Process for the production of optically active 2-halopropionic acids|
    US6903233B2|2002-03-11|2005-06-07|Takasago International Corporation|Process for producing optically active 3-halogenocarboxylic acid ester and 3-azidocarboxylic acid ester|
    JP2010047551A|2008-08-25|2010-03-04|Daicel Chem Ind Ltd|Method of preparing haloalkane carboxylate|
    CN103467334B|2013-09-03|2015-07-08|重庆工商大学|Synthesis method of N--propionyl-glutamine|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    FR7916335A|FR2459221B1|1979-06-20|1979-06-20|
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