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Synthetic method of clethodim

A synthetic method, the technology of clethodim, applied in the preparation of thioether, organic chemistry, etc., can solve the problems of high cost, difficulty in handling phosphine, and expensive Witting reagent, and achieve less solvent, less catalyst, and easy operation. simple effect

Active Publication Date: 2016-03-23
JIANGSU CHANGQING AGROCHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The Witting reagent in this method is expensive and expensive, and the phosphine generated by the reaction is difficult to handle

Method used

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  • Synthetic method of clethodim

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Experimental program
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Effect test

Embodiment 1

[0013] In the present invention, first add quantitative ethanethiol and crotonaldehyde into the addition reaction kettle, stir, and carry out addition reaction at normal temperature and pressure; then add quantitative ethyl acetoacetate and lye into the reaction kettle, stir and heat up to 70°C , kept at normal pressure for 10 hours to obtain ethylthioheptenone, after the reaction was completed, a mixture of toluene and water was added, allowed to stand for stratification, the waste water was discharged into the waste water treatment system, and the organic layer was transferred into the closed-loop reactor.

[0014] Add an appropriate amount of diethyl malonate and sodium ethoxide into the ring-closing reactor, stir and heat up to about 100°C, and react for about 6 hours under toluene reflux to obtain a ring compound. The ethanol produced by the reaction is recovered after secondary condensation, and the non-condensable gas is discharged through the exhaust pipe. After the ri...

Embodiment 2

[0018] 1) First, add ethanethiol and crotonaldehyde into the addition reaction kettle, stir, and carry out the addition reaction at normal temperature and pressure; then add ethyl acetoacetate and lye into the reaction kettle, stir and raise the temperature to 70°C, and under normal pressure Insulate for 11 hours to obtain ethylthioheptenone. After the reaction, add a mixture of toluene and water, let it stand for stratification, discharge the waste water into the waste water treatment system, and transfer the organic layer to the closed-loop reactor;

[0019] 2) Add diethyl malonate and sodium ethoxide into the closed-loop reaction kettle, stir and heat up to 90°C, and react for 7 hours under the reflux of toluene to obtain the ring compound; the ethanol produced by the reaction is recovered after secondary condensation and does not condense The gas is discharged through the exhaust tube; after the closed-loop reaction is completed, it is cooled to 35°C, and propionyl chloride...

Embodiment 3

[0023] The present invention carries out according to the following steps:

[0024] 1) First, add ethanethiol and crotonaldehyde into the addition reaction kettle, stir, and carry out the addition reaction at normal temperature and pressure; then add ethyl acetoacetate and lye into the reaction kettle, stir and raise the temperature to 60 ° C, under normal pressure Insulate for 12 hours to obtain ethylthioheptenone. After the reaction, add a mixture of toluene and water, let it stand for stratification, discharge the waste water into the waste water treatment system, and transfer the organic layer to the closed-loop reactor;

[0025] 2) Add diethyl malonate and sodium ethoxide into the closed-loop reaction kettle, stir and heat up to 105°C, and react for 7 hours in the state of toluene reflux to obtain the ring compound; the ethanol produced by the reaction is recovered after secondary condensation and does not condense The gas is discharged through the exhaust tube; after the...

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Abstract

Provided is a synthetic method of clethodim. The invention relates to cyclohexenone herbicide clethodim, namely, 2-(1-(((3-chloro-2-propenyl)oxy)imino)propyl)-5-(2-(ethylthio)propyl)-3-hydroxy-2-cyclohexene-1-one. A chain reaction is conducted on ethanethiol, crotonaldehyde, ethyl acetoacetate, ethylsuleenyl heptenone and propionyl chloride which serve as main raw materials and a trace catalyst to generate the clethodim. The synthetic method of the clethodim is green, environmentally friendly and high in economic benefit.

Description

technical field [0001] The present invention relates to cyclohexenone herbicide clethodim, namely (±)-2-[(E)-3-chloroallyloxyimino]propyl-5-[2-(ethylthio) Propyl]-3-hydroxycyclohex-2-enone synthesis process. Background technique [0002] The traditional process of synthesizing clethodim is to use Witting reagent and complete through Witting reaction, with a yield of 95%. The Witting reagent in this method is expensive and expensive, and the phosphine generated by the reaction is difficult to handle. Contents of the invention [0003] The technical scheme that the present invention adopts for this reason is: the present invention carries out according to the following steps: [0004] 1) First add ethanethiol and crotonaldehyde into the addition reaction kettle, stir, and carry out the addition reaction at normal temperature and pressure; then add ethyl acetoacetate and lye into the reaction kettle, stir and heat up to 60-80°C, Press down and keep warm for 8-12 hours to...

Claims

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Application Information

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IPC IPC(8): C07C323/47C07C319/20
CPCC07C319/20C07C323/47
Inventor 于国权丁华平马长庆袁宇
Owner JIANGSU CHANGQING AGROCHEMICAL CO LTD
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