New method for synthesizing fenoxaprop-P-ethyl

A technology for the synthesis of fenoxaprop-ethyl and its synthesis method, which is applied in the field of herbicide synthesis, can solve the problems of many by-products, large pollution, and low yield, and achieve products with high optical activity, high optical content, and high chemical content. Effect

Active Publication Date: 2012-02-15
JIANGSU FLAG CHEM IND
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The purpose of the invention is to overcome the existing method of using R-(+)-2-(4-hydroxyphenoxy) ethyl propionate and 2,6-dichlorobenzoxazole as raw material to react synthetic fenoxacarb Existing yield is not high in the method of spirit, reaction difficulty, by-product is many and waste water amount is big, the defects such as big pollution, provide a kind of new synthetic method of fenoxaprop-ethyl

Method used

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  • New method for synthesizing fenoxaprop-P-ethyl
  • New method for synthesizing fenoxaprop-P-ethyl
  • New method for synthesizing fenoxaprop-P-ethyl

Examples

Experimental program
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Embodiment 1

[0025] In a 500ml four-necked flask, drop into 200ml toluene, 21gR-(+)-2-(4-hydroxyphenoxy) ethyl propionate (0.1mol), 1.05g polyethylene glycol 600 and 17.4g anhydrous potassium carbonate ( 0.125mol), start stirring and mix at a stirring speed of 200rmp, heat up to 50°C while stirring until completely dissolved, add 19.7g of 2,6-dichlorobenzoxazole (0.105mol) dropwise at 60-65°C After about 2 hours of dripping, after the dripping, keep warm at 60-65°C for 6 hours, cool to room temperature and filter after the reaction, wash the filtrate with 2*50g water, let stand to separate the lower water layer, and distill the organic layer under reduced pressure The toluene was directly recovered and used mechanically, and the crude product was precipitated, and recrystallized with ethanol to obtain 35.46 g of refined oxaprop-ethyl white needle-like crystals, with a melting point of 80-84 ° C, a product purity of 98.95%, an effective optical body content of 99.7%, and a molar yield of the...

Embodiment 2

[0027] Drop into 200ml toluene, 21gR-(+)-2-(4-hydroxyphenoxy) ethyl propionate (0.1mol), 1.05 gram polyethylene glycol 6000 and 17.4g anhydrous potassium carbonate ( 0.125mol), start stirring and mix at a stirring speed of 200rmp, heat up to 50°C while stirring until completely dissolved, add 19.7g of 2,6-dichlorobenzoxazole (0.105mol) dropwise at 60-65°C , about 2 hours to drop, after the drop, keep warm at 60-65°C for 6 hours, cool to room temperature and filter after the reaction, wash the filtrate with 2*50g water, stand at 50°C to separate the lower water layer, and depressurize the organic layer The toluene was distilled and directly recovered and used mechanically. The crude product was precipitated and recrystallized with ethanol to obtain 35.27 g of white needle-like crystals of fenoxaprop-ethyl, with a melting point of 80-84 ° C, a product purity of 99.1%, and an effective optical body content of 99.5%. The product The molar yield is 96.58% (based on R-(+)-2-(4-hydro...

Embodiment 3

[0029] In a 500ml four-necked flask, drop 200ml of dichloroethane, 21g of R-(+)-2-(4-hydroxyphenoxy) ethyl propionate (0.1mol), 1.05 grams of polyethylene glycol 6000 and 17.4g of anhydrous Potassium carbonate (0.125mol), start stirring and mix at a stirring speed of 200rmp, heat up to 50°C while stirring until it dissolves completely, add 19.7g of 2,6-dichlorobenzoxazole ( 0.105mol), drop it in about 2 hours, keep it warm at 60-65°C for 6 hours after the drop, cool to room temperature and filter after the reaction, wash the filtrate with 2*50g water, let it stand to separate the lower water layer, and decompress the organic layer Ethylene dichloride was distilled and directly recovered and used mechanically. The crude product was precipitated and recrystallized with ethanol to obtain 35.3 g of refined fenoxaprop-ethyl white needle crystals with a melting point of 80-84°C. The product had a purity of 99.5% and an effective optical body content of 99% %, the product molar yield...

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Abstract

The invention discloses a new method for synthesizing fenoxaprop-P-ethyl. The method comprises the following steps of: dissolving ethyl R-(+)-2-(4-hydroxyphenoxy)propionate in an inert organic solvent, adding an acid binding agent potassium carbonate and a catalyst polyethylene glycol, stirring and mixing at the temperature of between 20 and 55DEG C, heating, slowly adding 2,6-dichlorobenzoxazole, keeping the temperature for reaction, filtering, evaporating the inert organic solvent for direct recovery and mechanical application, separating out a crude product, and recrystallizing to obtain the fenoxaprop-P-ethyl, wherein the inert organic solvent is one or more of benzene, methylbenzene, chlorobenzene and dichloroethane. The synthesis method only requires one-step reaction, the synthesiscost is saved, the preparation product has the advantages of high yield, high purity, high rotary content and the like, the pollution is light, and the recovered solvent can be directly applied to production mechanically. The fenoxaprop-P-ethyl has high market competitiveness and can meet the requirements of high-end markets at home and abroad.

Description

technical field [0001] The present invention relates to a kind of synthetic method of herbicide, especially relate to a kind of new synthetic method of fenoxaprop-ethyl. Background technique [0002] Fenoxaprop-p-ethyl is a heterooxyloxyphenoxypropionic acid herbicide, which mainly inhibits the synthesis of fatty acids by inhibiting the key enzyme acetyl-CoA carboxylase in fatty acid synthesis. The drug is absorbed and transmitted to the meristem and the growth point of the root through the stem and leaf, and the effect is rapid. After 2-3 days of application, the growth stops, and the heart leaves turn green and purple in 5-6 days, the meristem turns brown, and the leaves gradually die. A highly selective stem and leaf treatment agent. [0003] At present, the general industrialized production route of fenoxaprop-methyl-ethyl is mainly as follows: the product is obtained by reacting 2,6-dichlorobenzoxazole with hydroquinone, and the obtained product is mixed with ethyl p-t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/58
Inventor 王凤云剧宗峰陈晨吴耀军
Owner JIANGSU FLAG CHEM IND
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