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Method for synthesizing benzofuranone by taking o-chlorotoluene as raw material

A technology of benzofuranone and o-chlorotoluene, which is applied in the field of preparation of pharmaceutical intermediates, can solve the problems of harsh synthesis conditions, increased environmental pollution pressure, harsh conditions, etc., achieve high product yield and purity, and solve the problems of high raw material prices, high The effect of mild reaction conditions

Active Publication Date: 2020-05-19
安徽中羰碳一工业技术有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] But this method has cumbersome steps, harsh synthesis conditions and low yield
[0008] 2. Using anisole as a raw material, o-hydroxybenzoic acid is recyclized to generate benzofuranone, but in this process, the preparation process of o-hydroxybenzoic acid is complicated and the yield is very low, so it cannot be effectively promoted
[0009] 3. Using o-hydroxyphenylacetic acid as a raw material, benzofuranone is generated under the action of concentrated sulfuric acid catalyst, but this method is not only difficult to obtain raw materials, but also difficult to control the contact degree of concentrated sulfuric acid catalyst and raw materials, and it is easy to make o-hydroxybenzene Acetic acid is carbonized, the yield is low, and the concentrated sulfuric acid is severely corrosive to equipment, and the post-processing is complicated
[0010] It can be seen that the synthesis yield of existing benzofuranone is generally low and the conditions are harsh, and the operation is cumbersome, which not only causes a large amount of waste of raw materials and energy, but also increases the pressure of environmental pollution. It is urgent to improve the preparation process and seek for benzofuranone. Effective way with high yield and easy operation

Method used

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  • Method for synthesizing benzofuranone by taking o-chlorotoluene as raw material
  • Method for synthesizing benzofuranone by taking o-chlorotoluene as raw material
  • Method for synthesizing benzofuranone by taking o-chlorotoluene as raw material

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Experimental program
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Effect test

Embodiment 1

[0045] A kind of method taking ortho-chlorotoluene as raw material synthetic benzofuranone, its synthetic route is as follows:

[0046]

[0047] Specifically include the following steps:

[0048] (1), 12.6g (100mmol) of o-chlorotoluene, 1.84g (40mmol) of ethanol, 5.84g (40mmol) of tert-butyl peroxyether, Pd(Xantphos)Cl 2Add 15.2mg into the reaction kettle, feed carbon monoxide to 10atm, raise the temperature to 80°C, stir and react for 24 hours, maintain the carbon monoxide pressure at 10atm during the reaction, cool to room temperature after the reaction, discharge carbon monoxide, wash with sodium bisulfite aqueous solution, and dry , the raw material is recovered by distillation, and the organic phase after distillation is obtained for subsequent use;

[0049] (2), add 20mL of 6mol / L sodium hydroxide aqueous solution to the organic phase after the distillation that step (1) obtains, heat to 100 ℃ and stir reaction 2h, after reaction finishes, cool to room temperature, a...

Embodiment 2

[0052] A kind of method taking ortho-chlorotoluene as raw material synthetic benzofuranone, its synthetic route is as follows:

[0053]

[0054] Specifically include the following steps:

[0055] (1), 12.6g (100mmol) of o-chlorotoluene, 1.84g (40mmol) of ethanol, 5.84g (40mmol) of tert-butyl peroxyether, copper fluoride (0.6mg), and Xantphos (2.9mg) were added to the reaction kettle , feed carbon monoxide to 50atm, raise the temperature to 120°C, stir and react for 16 hours, maintain the carbon monoxide pressure at 50atm during the reaction, cool to room temperature after the reaction, discharge carbon monoxide, wash with sodium bisulfite aqueous solution, dry, and distill to recover the raw materials to obtain distilled The last organic phase is standby;

[0056] (2), add 20mL of 6mol / L sodium hydroxide aqueous solution to the organic phase after the distillation that step (1) obtains, heat to 170 ℃ and stir reaction 2h, cool to room temperature after reaction finishes, a...

Embodiment 3

[0059] A kind of method taking ortho-chlorotoluene as raw material synthetic benzofuranone, its synthetic route is as follows:

[0060]

[0061] Specifically include the following steps:

[0062] (1), 12.6 g (100 mmol) of o-chlorotoluene, 1.84 g (40 mmol) of ethanol, 5.84 g (40 mmol) of tert-butyl peroxide, ruthenium trichloride (1.1 mg), and Xantphos (2.9 mg) were added to the reaction kettle, Introduce carbon monoxide to 50 atm, raise the temperature to 150°C, stir and react for 10 hours, maintain the pressure of carbon monoxide at 50 atm during the reaction, cool to room temperature after the reaction, discharge carbon monoxide, wash with sodium bisulfite aqueous solution, dry, and distill to recover raw materials to obtain distilled The organic phase is ready for use;

[0063] (2), add 20mL of 6mol / L aqueous sodium hydroxide solution to the organic phase obtained in step (1), heat to 200°C and stir for 2h, cool to room temperature after the reaction, and adjust the pH ...

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Abstract

The invention provides a method for synthesizing benzofuranone by taking o-chlorotoluene as a raw material. According to the method, the target product benzofuranone is prepared by taking the easily-available o-chlorotoluene as the initial raw material, and the whole preparation process is mild in condition, high in yield and suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of preparation of pharmaceutical intermediates, in particular to a method for synthesizing benzofuranone by using o-chlorotoluene as a raw material. Background technique [0002] As an important intermediate in organic synthesis, benzofuranone is a kind of lactone compound widely present in natural and non-natural products. It is a compound with strong biological activity. It has been widely used in pesticides, medicines and new antioxidants. research hotspot. A large number of new fine chemicals can be derived from benzofuranone, for example, it can be used as an intermediate for the synthesis of azoxystrobin. Azoxystrobin is a very influential new type of agricultural fungicide in the pesticide industry. Almost all fungal pests have good activity, and have excellent protection, treatment, eradication, penetration, systemic activity and other characteristics. At present, the domestic production of azoxyst...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/83
CPCC07D307/83Y02P20/584
Inventor 刘显伟马青松马心旺魏力璟孙东艳朱华志赖彭莹
Owner 安徽中羰碳一工业技术有限责任公司
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