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Preparation method of (E)-2-methyl-alpha-methoxyimino methyl phenylacetate and intermediate thereof

A technology of hydroxyliminophenylacetonitrile and hydroxyliminobenzene, which is applied in the field of preparation of methyl-2-methyl-α-methoxyiminophenylacetate and its intermediates, can solve the problem of harsh operating conditions, A lot of waste water, high production cost and other problems, to achieve the effect of mild reaction conditions, shorten the reaction steps, and reduce the preparation cost

Pending Publication Date: 2021-05-28
JIANGXI TIANYU CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0029] In summary, the existing publicly disclosed technologies for the synthesis of compound (II) have disadvantages such as high cost of raw materials, high toxicity, harsh operating conditions, low yield, and a lot of waste water, which lead to high production costs of compound (II), resulting in oxime The production cost of strobilurin is relatively high, so the market competitiveness needs to be improved

Method used

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  • Preparation method of (E)-2-methyl-alpha-methoxyimino methyl phenylacetate and intermediate thereof
  • Preparation method of (E)-2-methyl-alpha-methoxyimino methyl phenylacetate and intermediate thereof
  • Preparation method of (E)-2-methyl-alpha-methoxyimino methyl phenylacetate and intermediate thereof

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Embodiment 1

[0059] In the present embodiment, 2-methyl-alpha-hydroxyiminophenylacetic acid is synthesized, and its method is as follows:

[0060] 88.9g (0.43mol) of 2-methyl-α-hydroxyiminophenylacetonitrile, add 150g of water, 21.5g of sodium hydroxide (0.52mol, content 96%), heat up to reflux reaction for 4 hours, cool down to about 10°C 110.6g (mass fraction 37%) of concentrated hydrochloric acid was cooled to about 5°C, and the reaction solution was added dropwise, and after the addition was completed, stirring was continued at 5-10°C for 1 hour, filtered, and the filter cake was rinsed with cold water and dried to obtain 75.6 g2-Methyl-α-hydroxyiminophenylacetic acid (the product is a mixture of Z configuration and E configuration, according to the peak areas of the two isomers in high performance liquid chromatography, the Z / E ratio is 5 / 94) , HPLC quantitative analysis, content 98.8%, yield 97.0%, melting point: 137-139°C. 1 H-NMR (D 6 -DMSO), δ:2.26(s, 3H, Ar-CH 3 ), 7.19-7.41 (...

Embodiment 2

[0062] In the present embodiment, 2-methyl-alpha-hydroxyiminophenylacetic acid is synthesized, and its method is as follows:

[0063] 88.9g (0.43mol) 2-methyl-α-hydroxyiminophenylacetonitrile, add 150g of water, 33.0g (0.86mol, content 96%) of sodium hydroxide, heat up to 60°C for 24 hours, then cool down to 10°C About; 149.3g of concentrated hydrochloric acid (mass fraction 37%) was cooled to about 5°C, added dropwise to the reaction solution, and after the addition was completed, continued to stir at 5-10°C for 1 hour, filtered, and the filter cake was rinsed with cold water and dried to obtain 74.6g 2-methyl-α-hydroxyiminophenylacetic acid (the product is a mixture of Z configuration and E configuration, Z / E ratio 3 / 96), HPLC quantitative analysis, content 99.0%, yield 96.0%

Embodiment 3

[0065] In the present embodiment, 2-methyl-alpha-hydroxyiminophenylacetic acid is synthesized, and its method is as follows:

[0066] 88.9g (0.43mol) 2-methyl-α-hydroxyiminophenylacetonitrile, add water 150g, sodium hydroxide 15.0g (0.39mol, content 96%), heat up to reflux reaction for 8 hours, cool down to about 10°C 110.6g (mass fraction 37%) of concentrated hydrochloric acid was cooled to about 5°C, and the reaction solution was added dropwise, and after the addition was completed, stirring was continued at 5-10°C for 1 hour, filtered, and the filter cake was rinsed with cold water and dried to obtain 73.9 g 2-methyl-α-hydroxyiminobenzene (Z / E mixture, Z / E ratio 4 / 95), HPLC quantitative analysis, content 98.9%, yield 95.0%.

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Abstract

The invention provides a preparation method of (E)-2-methyl-alpha-methoxyimino methyl phenylacetate and an intermediate thereof, and the intermediate 2-methyl-alpha-hydroxyimino phenylacetic acid is prepared by taking 2-methyl-alpha-hydroxyimino phenylacetonitrile as a raw material, carrying out hydrolysis reaction in the presence of an alkaline substance, and then acidifying to obtain the 2-methyl-alpha-hydroxyimino phenylacetic acid. According to the method, 2-methyl-alpha-hydroxyimino phenylacetic acid is taken as the raw material and reacts with a methylation reagent in the presence of an alkaline substance, and (E)-2-methyl-alpha-methoxyimino methyl phenylacetate is obtained. According to the method, 2-methyl-alpha-hydroxyimino phenylacetonitrile is used as the raw material, 2-methyl-alpha-hydroxyimino phenylacetic acid is generated through hydrolysis, the operation is simple, the cost is low, the reaction condition is mild, and the yield is high. In the preparation process of (E)-2-methyl-alpha-methoxyimino methyl phenylacetate, methylation of hydroxyl and esterification of carboxyl are completed by adopting a one-pot method, so that the operation is simplified, the reaction yield is high, and the cost is low.

Description

Technical field [0001] The invention belongs to the technical field of fungicides and relates to a preparation method of (E)-2-methyl-α-methoxyiminophenylacetic acid methyl ester and its intermediates. Background technique [0002] Trifloxystrobin (shown as formula (III)) is a highly efficient, broad-spectrum, low-toxic, environmentally friendly methoxyacrylate fungicide developed by Syngenta and Bayer of Germany. It has now become Hot spots in fungicide research. Among the existing trifloxystrobin synthesis processes, the process routes suitable for industrial production are basically the same. They are all obtained by condensation of 2-halomethyl-α-methoxyiminophenylacetic acid methyl ester and m-trifluoromethylacetophenone oxime. , as shown in Route 1. [0003] [0004] 2-Halomethyl-α-methoxyiminophenylacetic acid methyl ester is mainly prepared from compound (E)-2-methyl-α-methoxyiminophenylacetic acid methyl ester, and its structure is as formula (Ⅱ) As shown, bro...

Claims

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Application Information

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IPC IPC(8): C07C249/12C07C251/48C07C249/04
CPCC07C249/12C07C249/04C07C251/48
Inventor 向顺黄超群张荣罗亮明朱锦涛
Owner JIANGXI TIANYU CHEM CO LTD
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