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Method for synthesizing benzofuran-2 (3H)-ketone

A technology of benzofuran and compounds, which is applied in the field of synthesis of benzofuran-2(3H)-one, can solve the problems of high cost and complicated process, and achieve cost saving, shortening of synthesis steps and improvement of market competitiveness Effect

Pending Publication Date: 2022-05-13
JIANGSU CHANGQING AGROCHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] There are many reports on the synthesis of benzofuran-2(3H)-one at home and abroad, each has its own advantages, but the general process is complicated and the cost is high, which needs further improvement

Method used

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  • Method for synthesizing benzofuran-2 (3H)-ketone
  • Method for synthesizing benzofuran-2 (3H)-ketone
  • Method for synthesizing benzofuran-2 (3H)-ketone

Examples

Experimental program
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Effect test

Embodiment 1

[0050] Embodiment 1, the preparation of o-chlorophenylacetonitrile (OCBN)

[0051] Take a clean reaction bottle, add 5g of catalyst (benzyltriethylammonium chloride) and 270g (1.69mol) of o-chlorochloroben (OCBC) at room temperature, and stir to raise the temperature to 80°C. Add 85g (1.741mol) of 30% sodium cyanide aqueous solution dropwise, the dropping temperature is 80°C, and the drop is completed in about 6-7 hours. After the reaction is qualified, static layering. The water layer goes to the cyanide-containing wastewater treatment device, the oil layer is washed and stratified, and the water layer goes to the cyanide-containing wastewater treatment device. The oil layer is dedistilled, the vacuum degree is controlled not lower than -0.098MPa, and the temperature is not higher than 135°C to obtain the intermediate o-chlorophenylacetonitrile. Yield 95%.

Embodiment 2

[0052] Embodiment two, the preparation of o-chlorophenyl acetate sodium (OCPANa)

[0053] Add 270g (2.15mol) of sodium hydroxide solution to a clean round-bottomed flask, stir and raise the temperature to 110°C, keep the reflux state, add the intermediate OCBN (1.845mol) dropwise, and the dropwise addition ends in about 4 to 5 hours , after the sampling analysis is qualified, and after the reaction is qualified, the material is dried to obtain solid sodium o-chlorophenylacetate (OCPANa). The ammonia gas produced is absorbed by spraying with aqueous solution containing sulfuric acid. Yield 100%.

Embodiment 3

[0054] Embodiment three, the preparation of o-hydroxyphenylacetic acid (OHPAA)

[0055] At room temperature, add 180g (0.943mol) of the intermediate (OCPANa) dried product, 3g of catalyst copper acetate, and 320g (2.59mol) of liquid caustic soda into the autoclave to dissolve, stir and raise the temperature to 220°C, keep it warm for 2 hours, solution reaction. The pressure is controlled at 1.5-2.1MPa. After the reaction was completed, the temperature was lowered to 110-120°C. Empty, add 80mL of water, filter, and recover the catalyst. The centrifuged mother liquor is transferred to another clean bottle, and 160 g of hydrochloric acid is added for neutralization. The neutralization solution was lowered to room temperature and filtered. The filter cake is washed with water and filtered, and the filter cake is the intermediate o-hydroxyphenylacetic acid (OHPAA). Yield 90%.

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Abstract

The invention discloses a synthesis method of benzofuran-2 (3H)-ketone, and relates to preparation of benzofuran-2 (3H)-ketone in organic chemistry. The method comprises the following steps: reacting o-chlorobenzyl chloride serving as a raw material with sodium cyanide under the action of a catalyst to obtain OCBN; then reacting the OCBN with sodium hydroxide to obtain OCPANa; then carrying out strong alkali and high-temperature hydrolysis on the OCPANa in the presence of a catalyst under a certain pressure to obtain disodium salt (OHPAA), and acidifying to obtain OHPAA. And finally, carrying out ring-closure reaction on the (OHPAA) in the presence of a catalyst, carrying out toluene azeotropic dehydration, and then carrying out alkali washing, water washing, desolvation and distillation to obtain the benzofuran-2 (3H)-ketone. According to the present invention, with the benzofuran-2 (3H)-ketone synthesis route, the synthesis steps of the traditional process are shortened, the cost is saved for the future industrial production, and the market competitiveness of the benzofuran-2 (3H)-ketone is effectively improved.

Description

technical field [0001] The invention relates to organic synthesis reactions, in particular to a synthesis method of benzofuran-2(3H)-one. Background technique [0002] Benzofuran-2(3H)-ketone (2-Coumaranone) is an important organic intermediate, which can be used in medicine, pesticides and new antioxidants. Especially the main raw material of the pesticide fungicide azoxystrobin. [0003] There are many reports on the synthesis of benzofuran-2(3H)-one at home and abroad, and each has its own advantages. However, the general process is complicated and the cost is high, which needs further improvement. Contents of the invention [0004] The present invention is by the analysis to traditional technology, has researched with o-chlorobenzyl chloride as raw material and sodium cyanide, reacts under catalyst action to obtain OCBN; Reuse OCBN and sodium hydroxide reaction, obtain OCPANa; Intermediate OCPANa exists certain Under the condition of pressure, disodium salt (OHPAA) c...

Claims

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Application Information

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IPC IPC(8): C07D307/83
CPCC07D307/83
Inventor 于国权周兴军马长庆丁华平
Owner JIANGSU CHANGQING AGROCHEMICAL CO LTD
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