Preparation method for 2-methylmercapto-4-thrifluoromethyl benzoate

A technology of methyl trifluoromethyl benzoate and trifluoromethyl benzonitrile, which is applied in the field of preparation of methyl 2-methylthio-4-trifluoromethyl benzoate, can solve the problem of high raw material cost and reaction conditions Harsh, unfriendly to the environment, etc., to achieve the effect of reducing the treatment of three wastes, shortening the reaction steps, and reducing the discharge of three wastes

Inactive Publication Date: 2015-09-23
HUNAN HAILI CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] In summary, it is very difficult to invent a new method for synthesizing 2-methylthio-4-trifluoromethylbenzoic acid methyl ester by changing the raw material cost that exists in the traditional synthetic route. Needed

Method used

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  • Preparation method for 2-methylmercapto-4-thrifluoromethyl benzoate
  • Preparation method for 2-methylmercapto-4-thrifluoromethyl benzoate

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Embodiment 1

[0024] Add 100ml methanol in the reaction flask, then add 21.7g (0.1mol) 2-methylthio-4-trifluoromethylbenzonitrile, then add 22.6g90% aqueous sulfuric acid, heat the mixture at 80°C for 10 hours, and then The reaction solution was distilled to remove solvent methanol, the concentrated solution was washed with water, filtered, and dried to obtain 24.8g (0.0983mol) 2-methylthio-4-trifluoromethylbenzoic acid methyl ester, content 99.1%, yield 98.3% ( Calculated as 2-methylthio-4-trifluoromethylbenzocyanide).

Embodiment 2

[0026] Add 100ml of methanol in the reaction flask, then add 21.7g (0.1mol) 2-methylthio-4-trifluoromethylbenzonitrile, then add 22.6g of 60% sulfuric acid aqueous solution, after heating the mixture at 80°C for 10 hours, the The reaction solution evaporated methanol, and the concentrated solution was washed with water, filtered, and dried to obtain 24.7g (0.0967mol) 2-methylthio-4-trifluoromethylbenzoic acid methyl ester, content 97.9%, yield 96.7% (with 2- Methylthio-4-trifluoromethylbenzocyanide).

Embodiment 3

[0028] Add 100ml of methanol in the reaction flask, then add 21.7g (0.1mol) 2-methylthio-4-trifluoromethylbenzonitrile, then add 22.6g of 30% aqueous sulfuric acid, and heat the mixture at 80°C for 10 hours, The reaction solution was evaporated to methanol, the concentrated solution was washed with water, filtered and dried to obtain 24.0g (0.0933mol) 2-methylthio-4-trifluoromethylbenzoic acid methyl ester, content 97.2%, yield 93.3% (with 2 -methylthio-4-trifluoromethylbenzocyanide).

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Abstract

The invention discloses a preparation method for 2-methylmercapto-4-thrifluoromethyl benzoate. The method comprises the following steps: using 2-methylmercapto-4-trifluoromethylbenzonitrile as a raw material; then under atmospheric pressure, carrying out hydrolysis and esterification reactions with methanol as the raw material and a solvent under acid condition provided by a H2SO4 aqueous solution; and using a one-pot method so as to prepare 2-methylmercapto-4-thrifluoromethyl benzoate, wherein the 2-methylmercapto-4-thrifluoromethyl benzoate has a mass content of 96.8% to 99.2% and a yield of 92.9% to 98.5%, and has a reaction formula as shown in the specification. The preparation method provided by the invention improves and innovates synthetic raw materials and reaction conditions; and 2-methylmercapto-4-thrifluoromethyl benzoate is prepared by directly subjecting 2-methylmercapto-4-trifluoromethylbenzonitrile to hydrolysis and esterification reactions under the acid condition; thus, three-wastes treatment and three-wastes discharge are reduced; process operation flow is simplified; reaction steps are shortened; and reaction conversion rate and selectivity can reach more than 90%.

Description

technical field [0001] The present invention relates to the preparation method of 2-methylthio-4-trifluoromethylbenzoic acid methyl ester. Background technique [0002] Methyl 2-methylthio-4-trifluoromethylbenzoate is an intermediate of the herbicide isoxaflutole, and its molecular structure is: [0003] [0004] Isoxaflutole belongs to the para-hydroxyphenylpyruvate dioxygenase inhibitors (HPPD inhibitors). It is used for soil treatment in upland crop fields such as corn and sugar cane. It is a selective systemic pre-emergence herbicide of organic heterocycles, which works mainly through the absorption and conduction of weed young roots. After absorption by sensitive weeds, the formation of chlorophyll can be destroyed by inhibiting p-hydroxypropiophenone dioxygenase, resulting in chlorosis and wilting of harmful weeds, and finally achieves the purpose of selective weeding. [0005] The preparation method of the reported 2-methylthio-4-trifluoromethylbenzoic acid methy...

Claims

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Application Information

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IPC IPC(8): C07C323/62C07C319/20
Inventor 全春生王燕罗先福李萍臧阳陵王宇
Owner HUNAN HAILI CHEM IND
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