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Preparation method of ortho/para-substituted phenylformic acid compound

A technology of benzoic acids and compounds, which is applied in the field of preparation of benzoic acid compounds, can solve problems such as low reaction yield and difficult product separation, and achieve the effects of good purity, shortened reaction time, and high product yield

Active Publication Date: 2009-11-11
NUTRICHEM LAB CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the trifluoromethyl group on the benzene ring is unstable under acidic and high temperature conditions, the above process usually produces a certain amount of by-product 2-nitroterephthalic acid, resulting in low reaction yield and difficult product separation.

Method used

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  • Preparation method of ortho/para-substituted phenylformic acid compound
  • Preparation method of ortho/para-substituted phenylformic acid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1 Preparation of 2-methylthio-4-trifluoromethylbenzoic acid

[0021] Add 4.4g (0.02mol) of 2-methylthio-4-trifluorobenzonitrile, 3.2g (0.08mol) of sodium hydroxide, 2mL of water, and 40mL of ethylene glycol to the reaction flask in sequence, start stirring, and heat to 140 ℃, reacted for 3 hours, and took samples for HPLC chromatographic detection and analysis. The reaction conversion rate was 99.6%, and the reaction selectivity was 98.3%. Cool down to 30°C, add 30%% hydrochloric acid to adjust the pH to 6, filter, wash the filter cake with 50mL of water, dry, weigh to obtain 4.4g, and the yield is 93.6%. 1 H NMR (500NMR, d 6 -acetone): δ 2.54 (s, 3H), 7.54 (q, 1H), 7.63 (s, 1H), 8.19 (d, 1H).

Embodiment 2

[0022] Example 2 Preparation of 2-methylthio-4-trifluoromethylbenzoic acid

[0023] Add 26.1g (0.12mol) of 2-methylthio-4-trifluorobenzonitrile, 27g (0.48mol) of potassium hydroxide, 10mL of water, and 100mL of glycerin to the reaction flask in sequence, start stirring, and heat to a temperature of 140°C , reacted for 3 hours, sampled for HPLC chromatographic detection and analysis, the reaction conversion rate was 97.3%, and the reaction selectivity was 99%. Cool down to 30°C, add 30% hydrochloric acid to adjust the pH value of the reaction solution to 6, filter, wash the filter cake with 200mL water, dry, weigh 27.2g, and the product yield is 96.1%.

Embodiment 3

[0024] Example 3 Preparation of 2-nitro-4-trifluoromethylbenzoic acid

[0025] Add 8.7g (0.04mol) of 2-nitro-4-trifluorobenzonitrile, 16g (0.28mol) of potassium hydroxide, 10mL of water, and 50mL of ethylene glycol in the reaction flask, start stirring, and heat to a temperature of 140 ℃, reacted for 4 hours, sampled for HPLC chromatographic detection and analysis, the reaction conversion rate was 98.6%, and the reaction selectivity was 99.2%. Cool down to 30°C, add 30% hydrochloric acid to adjust the pH of the reaction solution to 6, filter, wash the filter cake with 100 mL of water, dry, weigh to obtain 8.9 g, and the product yield is 94.7%. 1 H NMR (500NMR, CDCl 3 ): δ8.02(d, 1H), 8.07(q, 1H), 8.26(s, 1H).

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Abstract

The invention relates to a preparation method of an ortho / para-substituted phenylformic acid compound with a general formula (I), wherein R1 and R2 are respectively or simultaneously C1-C3 sulfenyl, nitryl, CF3, C2F5 or C3F7 and other groups. The compound is obtained by conducting hydrolysis on a compound with a corresponding general formula (II) in an alkaline condition at the temperature controlled within a range of 80-180 DEG C for 1-6 h. The preparation method has the advantages of simple process, short reaction time, high reaction conversion rate and selectivity, high product purity and the like, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of ortho-para-substituted benzoic acid compounds. Background technique [0002] Benzoylisoxazole herbicides (benzoylisoxazole herbicides), such as isoxaflutole (isoxaflutole), pyrasulfotole, etc., are a class of broad-spectrum herbicides with a new mechanism of action. Enzyme inhibitors, by inhibiting the synthesis of p-hydroxyphenylpyruvate dioxygenase, lead to the accumulation of tyrosine, hinder the biosynthesis of plastoquinone and tocopherol, and then affect the biosynthesis of carotenoids. [0003] Ortho-substituted p-trifluoromethylbenzoic acid is one of the intermediates for the preparation of isoxaflutole and pyrasulfotole. This intermediate can be prepared by hydrolysis of ortho-substituted p-trifluoromethylbenzonitrile, as described in the literature J.A.C.S. Volume 76 (1954) pages 1051-1054 and patents US4868333, US4781750. Preparation of o-nitr...

Claims

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Application Information

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IPC IPC(8): C07C323/62C07C319/20C07C205/58C07C201/12
Inventor 彭阳王文军张政陈建伟母灿先刘世禄曹锦王曙光绵丽娟
Owner NUTRICHEM LAB CO LTD
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