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Preparation method of azoxystrobin intermediate

An intermediate, azoxystrobin technology, applied in the field of agricultural fungicides preparation, can solve problems such as long reaction time, low benzofuranone content, incomplete reaction, etc., achieves improved yield and purity, shortened reaction time, reduced The effect of production costs

Active Publication Date: 2011-11-16
JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this method, the required reaction time of the benzofuranone step synthesized from o-hydroxyphenylacetic acid is long, the reaction transformation is not complete, it is difficult to achieve the desired yield and purity, and at the same time, due to the low content of benzofuranone, it causes azimuth bacteria Lower overall yield of esters
Industrially, in the step of synthesizing benzofuranone from o-hydroxyphenylacetic acid, concentrated sulfuric acid is used as a catalyst. Although the reaction speed is accelerated to a certain extent, the reaction is still not complete, and about 5% of o-hydroxyphenylacetic acid cannot be converted It is benzofuranone, if it is not refined, it will be directly used in the next step reaction, which will affect the yield of azoxystrobin

Method used

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  • Preparation method of azoxystrobin intermediate

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Experimental program
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Effect test

Embodiment 1

[0017] The preparation of the azoxystrobin intermediate according to the present embodiment comprises the following three steps:

[0018] (1) Preparation of o-hydroxyphenylacetic acid

[0019] 173g (99%, 1.00mol) of o-chlorophenylacetic acid, 800g (12.5%, 2.5mol) of sodium hydroxide aqueous solution, 6.6g (98%, 0.1mol) of copper powder were put into the autoclave, and the pressure was slowly increased to 7KPa ( Relative to atmospheric pressure), heat preservation reaction at 160°C for 3 hours, after the reaction is completed, cool down and filter, recover copper powder, add hydrochloric acid to the mother liquor to adjust pH, freeze and filter to obtain o-hydroxyphenylacetic acid, 140g after drying, content 97.5%.

[0020] (2) Preparation of benzofuranone

[0021] Put 140g (97.5%, 0.90mol) of o-hydroxyphenylacetic acid, 2g (98%, 0.02mol) of concentrated sulfuric acid into a 1L reaction flask equipped with a condenser tube and a receiving flask, turn on the vacuum, a...

Embodiment 2

[0025] The preparation of the azoxystrobin intermediate according to the present embodiment comprises the following three steps:

[0026] (1) Preparation of o-hydroxyphenylacetic acid

[0027] 173g (99%, 1.00mol) of o-chlorophenylacetic acid, 800g (12.5%, 2.5mol) of sodium hydroxide aqueous solution, 10.2g (98%, 0.1mol) of cuprous chloride were put into the autoclave, and slowly pressurized to 7KPa (relative atmospheric pressure), heat preservation reaction at 160°C for 3 hours, after the reaction is completed, cool down and filter to recover cuprous chloride, add hydrochloric acid to adjust the pH of the mother liquor, freeze and filter to obtain o-hydroxyphenylacetic acid, 141g after drying, content 97.3%.

[0028] (2) Preparation of benzofuranone

[0029] 141g (97.3%, 0.90mol) o-hydroxyphenylacetic acid, 2g (98%, 0.02mol) methanesulfonic acid, put into a 1L reaction flask equipped with a condenser tube and a receiving flask, turn on the vacuum, when the pressure ...

Embodiment 3

[0033] The preparation of the azoxystrobin intermediate according to the present embodiment comprises the following three steps:

[0034] (1) Preparation of o-hydroxyphenylacetic acid

[0035] 173g (99%, 1.00mol) of o-chlorophenylacetic acid, 800g (12.5%, 2.5mol) of sodium hydroxide aqueous solution, 12.7g (98%, 0.1mol) of copper carbonate were put into the autoclave, and slowly pressurized to 7KPa ( Relative atmospheric pressure), heat preservation reaction at 160°C for 3 hours, after the reaction is completed, cool down and filter to recover copper carbonate, add hydrochloric acid to adjust the pH of the mother liquor, freeze and filter to obtain o-hydroxyphenylacetic acid, 140g after drying, content 97.4%.

[0036] (2) Preparation of benzofuranone

[0037] Put 140g (97.4%, 0.90mol) o-hydroxyphenylacetic acid, 2g (98%, 0.02mol) concentrated sulfuric acid into a 1L reaction flask equipped with a condenser tube and a receiving flask, turn on the vacuum, and when the...

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Abstract

The invention relates to a preparation method of an azoxystrobin intermediate. The method comprises the following steps of: (1) synthesizing benzofuranone from o-hydroxyphenylacetic acid serving as a raw material; and (2) making benzofuranone react with trimethyl orthoformate to generate the azoxystrobin intermediate, wherein no solvent is used in the reaction in the step (1); and the reaction isperformed by the following steps of: putting o-hydroxyphenylacetic acid and 0-3 percent of catalyst into a reaction kettle; preserving heat in vacuum at the temperature 125-180 DEG C to react for 2-3hours; and evaporating water generated by the reaction in vacuum, wherein the residue in the reaction kettle is benzofuranone. The method has the advantages of simple process, high yield of the azoxystrobin intermediate and low production cost.

Description

technical field [0001] The invention belongs to the technical field of preparation of agricultural fungicides, in particular to a preparation method of an azoxystrobin intermediate. Background technique [0002] Azoxystrobin is the abbreviation of E-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxymethyl acrylate. , Treatment, eradication, penetration, systemic activity, and a new type of methoxyacrylate fungicide that can be degraded quickly in plants, soil and water. Azoxystrobin can be used for stem and leaf treatment, seed treatment, and soil treatment. Its suitable crops are grains, rice, grapes, potatoes, vegetables, fruit trees, beans, etc. The experimental preparation of azoxystrobin uses o-hydroxyphenylacetic acid as the starting material, toluene as the solvent, acetic acid as the catalyst, reflux and cutting water for 4-6 hours, and the toluene is removed to obtain benzofuranone. Then react benzofuranone with trimethyl orthoformate to generate 3-(2-met...

Claims

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Application Information

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IPC IPC(8): C07D307/83
Inventor 余志强陶伟钱海滨李彩凤
Owner JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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