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

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Problems solved by technology

Because the trifluoromethyl group on the benzene ring is unstable under acidic and high temperature conditions, the above process usua

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

Example Embodiment

[0020] Example 1 Preparation of 2-methylthio-4-trifluoromethyl benzoic 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 into the reaction flask, start stirring, and heat to 140 After reacting for 3 hours at °C, samples were taken for HPLC chromatographic detection and analysis, the reaction conversion rate was 99.6%, and the reaction selectivity was 98.3%. The temperature was lowered to 30° C., 30%% hydrochloric acid was added to adjust the pH to 6, filtered, the filter cake was washed with 50 mL of water, dried, and weighed to obtain 4.4 g, with a yield of 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).

Example Embodiment

[0022] Example 2 Preparation of 2-methylthio-4-trifluoromethyl benzoic 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 in the reaction flask, start stirring, and heat to 140℃ After reacting for 3 hours, sampling and HPLC chromatographic analysis showed that the reaction conversion rate was 97.3%, and the reaction selectivity was 99%. The temperature was lowered to 30°C, 30% hydrochloric acid was added to adjust the pH value of the reaction solution to 6, filtered, the filter cake was washed with 200 mL of water, dried, weighed to obtain 27.2 g, and the product yield was 96.1%.

Example Embodiment

[0024] Example 3 Preparation of 2-nitro-4-trifluoromethyl benzoic 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 140 After reacting for 4 hours at °C, sampling and HPLC chromatographic detection and analysis showed that the reaction conversion rate was 98.6% and the reaction selectivity was 99.2%. The temperature was lowered to 30°C, 30% hydrochloric acid was added to adjust the pH value of the reaction solution to 6, filtered, the filter cake was washed with 100 mL of water, dried, weighed to obtain 8.9 g, and the product yield was 94.7%. 1 H NMR (500NMR, CDCl 3 ): δ 8.02 (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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