A kind of preparation method of 5-{2-(ethylthio)propyl}-3-hydroxyl-cyclohex-2-enone

A }-3-, ethylthio-based technology, applied in the field of preparation of pesticide intermediates, can solve problems such as increasing the difficulty of tail gas treatment, and achieve the effects of mild reaction process, reduced environmental impact, and high reaction yield

Active Publication Date: 2020-05-19
WEIFANG CYNDA CHEM
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

This process route not only requires the use of ethanethiol, which has a strong and long-lasting odor, but also uses ethanethiol as a raw material in the first step, resulting in the need to treat ethanethiol gas in the entire production process, which increases the difficulty of tail gas treatment.

Method used

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  • A kind of preparation method of 5-{2-(ethylthio)propyl}-3-hydroxyl-cyclohex-2-enone
  • A kind of preparation method of 5-{2-(ethylthio)propyl}-3-hydroxyl-cyclohex-2-enone
  • A kind of preparation method of 5-{2-(ethylthio)propyl}-3-hydroxyl-cyclohex-2-enone

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Embodiment 1

[0029] 1. Condensation reaction: Add 21.9g of 5-bromo-m-phenylene dimethyl ether into a 250ml four-necked bottle with a thermometer and a condenser tube {melting point 62-66°C; appearance: off-white solid; NMR: 1 H NMR (CDCl 3 ,400MHz) δ (ppm) data is as follows: 3.82 (s, 6H, CH 3 ), 6.37(t, 1H, Ar-H), 6.81(d, 2H, Ar-H)}, 12.8g bromopropylene, 20.4g triethylamine, 2.2g dppp nickel chloride, 130ml methyl tert-butyl ether , magnetically stirred, heated in an oil bath, kept warm for 4 hours when the temperature rose to 50°C, cooled to room temperature after the reaction, washed the reaction solution with 60ml of 10% hydrochloric acid aqueous solution, washed with water until neutral, and distilled the organic layer under reduced pressure to obtain 17.4g 5-propenyl-m-xylylene ether {melting point 97-100°C; appearance: white solid; NMR: 1 H NMR (CDCl 3 ,400MHz) δ (ppm) data is as follows: 3.23 (d, 2H, CH 2 ), 3.83 (s, 6H, CH 3 ), 4.91 (m, 2H, C=CH 2 ), 5.90 (m, 1H, C=C-H) 6.2...

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Abstract

The invention discloses a preparation method of 5-{2-(ethylthio) propyl}-3-hydroxy-hexanaphthene-2-ketene. The method belongs to a method generating 5-{2-(ethylthio) propyl}-3-hydroxy-hexanaphthene-2-ketene by using 5-bromine-m-dimethoxy benzene as raw materials through condensation reaction, addition reaction, substitution reaction, catalyzed hydrolysis, catalytic hydrogenation. The method provided by the invention has the advantages that the reaction procedure is simple; the reaction process is mild; the reaction yield is high; particularly, the use of ethanethiol is avoided; the influence on the environment can be effectively reduced; the production and the personnel safety of peripheral staff are ensured.

Description

technical field [0001] The invention belongs to the technical field of preparation of pesticide intermediates, in particular to a preparation method of 5-{2-(ethylthio)propyl}-3-hydroxyl-cyclohex-2-enone. Background technique [0002] 5-{2-(Ethylthio)propyl}-3-hydroxy-cyclohex-2-enone is an essential precursor of cyclohexenone herbicides clethodim and sethoxydim. Cyclohexenone herbicides are highly selective and can control a variety of grass weeds, including annual grass weeds and perennial grass weeds, and are safe for dicotyledonous crops. residual herbicides. [0003] At present, the main synthesis process of this product is: [0004] U.S. Patent No. 4,440,566 introduces that crotonaldehyde and ethanethiol are used as raw materials to react and synthesize 3-ethylthiobutyraldehyde, then react with acetoacetate sodium salt to obtain 6-ethylthio-3-ene-2-heptanone, and then react with acetoacetate Dimethyl diacid is condensed into a ring, and the target product (formula A...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/30C07C43/215C07C41/22C07C43/225C07C319/14C07C323/16C07C319/20C07C323/22
CPCC07C41/22C07C41/30C07C319/14C07C319/20C07C43/215C07C43/225C07C323/16C07C323/22
Inventor 李凯王广月杨齐伟邹亚波
Owner WEIFANG CYNDA CHEM
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