• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:

    公开号:SU934907A3
    申请号:SU792847446
    申请日:1979-11-29
    公开日:1982-06-07
    发明作者:Мишлэ Даниель；Ракутц Мишель
    申请人:Филагро(Фирма)；
    IPC主号:
    专利说明:

    The invention relates to a method for producing ortho-metalloxifenop, which is used in organic synthesis. A known method of producing orthometal; liloxazphenol, by reacting pyrocatechin with metaplyl chloride at a ratio of 1: (0.25-0.75) in an organic solvent that is not miscible with water (dimethyl sulfide, dimethyl formavd, acetonitrile) in the presence of an aqueous alkali solution at 70-120 C and the selection of the target product from the reaction mass by distillation of Cl. The disadvantage of this method is the formation of side cymegalpyl Xphenol (up to 5%), as well as a relatively low yield of the target product (71%). The circuit of the invention is an increase in the output of the helical product. The goal is achieved in that according to the method of obtaining orthometalyloxyphenol by reacting an excess of pyrocatechol with methyl chloride in two different zones, in the first zone, the initial reagents are mixed in the presence of tetrabutylammonium chloride and an aqueous alkali solution in anisole medium at 18 - 27 ° C, which formed the aqueous and organic layers are separated, the latter is directed to the second zone, heated in the presence of an aqueous alkali solution to 8–120 ° C, after cooling it is returned to the first zone, where additionally t or an aqueous solution of sodium hydroxide, or catechol and / or metallilhlrrid, then separated again the formed aqueous and organic layers, the latter directing $ sweat into the second zone is heated to 80 - 120RS, the resulting reaction mixture is acidified to yield a desired product. The yield of the target product is 89 - 91%, while the proposed method allows to avoid the formation of side dimetallyloxyphenol, as well as to reduce the formation of alkenylphenols (side reaction C-alkylene) to 0.08 - 0.7%. Example. In a flask A, equipped with a magnetic stirrer, it is charged at 70 cm with anisole degassed with argon. 16.5 g of pyrocatechol, 2O cm 5 etallylchlorond, 10 g of tetrabutyl ammonium chloride, an alkali aqueous solution obtained from 1.49 g of NqOH and 10 cm of water. When adding reagents temperature. rises to 21 ° C. The resulting mixture was stirred for 2O minutes, allowed to stand, then the organic phase was transferred to flask 6i identical to flask A containing argon. Heat the flask 5 for 30 m while cooling to room temperature and reintroduce the contents into flask A. Add (1) solution of 1.26 g of caustic soda in 5 cm of water to flask A and start the same cycle from the beginning: And a solution of 1.29 g of caustic soda in 5 cm of water is added, and the same cycle of operation is started a second time without reloading caustic soda between the two last works. Collect the contents of flask A and b, acidify to pH 4 ( aqueous phase) aqueous solution and sulfuric acid. As a result, 9.15 g of residual pyrocatechol is obtained and rectification is used to extract 10 g of ortho-metaplilicophenop (yield: 91.3% relative to the pyrocatechin converted), 0.08 g of ortho-methylpyrocatechin (yield: 0.7% relative to pyrocatechin converted to 0.08 g of ortho-metalpyrocatechin (yield 0.7% relative to the converted pyrocatechin) .Example 2. The flask A, equipped with a magnetic stirrer, is charged at 18 ° C with 350 cm anisole, 100 cm metallic chloride, 50 g tetrabutylammonium chloride, 45 g pyrocatechin, 50 cm of an aqueous solution containing 7.2 g of sodium hydroxide (N00H). The forehead A is stirred for 20 minutes, then decanted and the organic phase is transferred to flask b, where it is heated for 30 minutes at 1OOC cooled to room temperature, and the contents of flask B are introduced into flask A and then charged into flask A 16, 5 g of pyrocatechin and a solution of 6 g of caustic soda in 2 5 cm of water, and again start the same cycle of work without any intermediate load between these two operating cycles. As a result, 31.56 g of residual pyrocatechin are obtained (degree of conversion: 59.5 %), 61.5 g of ortho-metalloxyphenol (89% yield, with respect to pyrocatechin), 0.26 g of ortho-metalpyrocatechin (yield 0.4% relative to the converted pyrocatechin). PRI me R 3. A flask A, equipped with a magnetic stirrer, was charged at 18 ° C with 70 cm of anisole, 14.5 g of pyrocatechin, 10 g of tetrabutylammonium chloride, and 10 cm of aqueous solution containing 1.48 g of caustic soda. After stirring for 2 minutes, the organic phase is decanted and the organic phase is transferred to flask b; in which 10 cm of metal chloride is loaded and heated at 100 ° C for 30 minutes. After cooling, the contents of flask B are again transferred to flask D and three such cycles of operation are carried out successively. The table shows the amount of metal chloride introduced into flask 5 before heating. 5.78 g of residual pyrocatechol (degree of pretreatment 60.5%), 11.9 g of ortho-metalloxyphenol (yield 91% relative to the converted pyrocatechin) and 0.08 g orthometallylpyrocatechin (yield 0.6% in relation to the converted pyrocatechin). Example 4. A flask A equipped with a magnetic stirrer was charged at 18 ° C with 70 cm of anisole, 20 cm of methyl chloride, 10 g of tetraabutylammonium chloride, 9 g of pyrocatechin and 10 cm of aqueous solution containing 1.5 g of sodium hydroxide. After the ZO min. Stirring and decanting, the organic phase is transferred to flask B, for heating at 90 ° C for 1 h 30 min. After cooling, 3.27 g of pyrocatechol are added and dissolved, and the aggregate is again introduced into flask A, where it is stirred and, in addition, 1.19 g of sodium hydroxide dissolved in 5 cm of water are added. The working cycle is started again, taking into account that 3.38 g of pyrocatechin are added to the two last working cycles.
    in flask B and 1.26 g of sodium hydroxide (in S cm of water) in flask A.
    As a result, 6.67 g of residual pyrocatechol 12.11 g ort or tallyloxyphenol are obtained (yield 90.6% relative to the converted quinate pyroxide).
    权利要求:
    Claims (1)
    [1]
    1. French patent number 2255279, l. C O7 C 43/20, published. 1969 (prototype).
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    US4263462A|1981-04-21|
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    US3927118A|1973-12-21|1975-12-16|Crown Zellerbach Corp|Process for monoetherification of polyhydric benzenes|US4465868A|1981-07-17|1984-08-14|Otsuka Kagaku Yakuhin Kabushiki Kaisha|Process for preparing o-methallyloxyphenol|
    US4613703A|1982-04-05|1986-09-23|The Dow Chemical Company|Process for allylating hydroxyaromatic compounds|
    IT1151718B|1982-04-19|1986-12-24|Brichima Spa|PROCEDURE FOR THE PREPARATION OF 2,3-DIHYDRO-2,2-DIMETHYLBENZOFURAN-7-OLO|
    IT1196002B|1984-01-20|1988-11-10|Brichima Spa|PROCEDURE FOR THE SYNTHESIS OF O-ISOPROPOSSIPHENOL|
    KR910003821B1|1987-06-01|1991-06-12|더 다우 케미칼 캄파니|Process for preparing propargyl ethers of hydroxyaromatic compounds|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    FR7834297A|FR2442822B1|1978-11-30|1978-11-30|
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