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Preparation method of 2-alkyl -3-(4-hydroxybenzene formyl) benzfuran

A technology of hydroxybenzoyl and alkoxybenzoyl, which is applied in the field of preparing 2-alkyl-3-benzofuran, can solve the problems of low product yield, long reaction time, high impurities, etc., and achieve product yield Increased height, shortened reaction time, and increased purity

Inactive Publication Date: 2013-08-28
DEZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The main problem of the above preparation method is that the dealkylation reaction is too long due to the low temperature, the dealkylation reaction is not complete, and the product purity is not high; there is no acid hydrolysis and pickling steps in the dealkylation reaction product process, This will cause incomplete dealkylation reaction, resulting in low product yield and high impurities

Method used

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  • Preparation method of 2-alkyl -3-(4-hydroxybenzene formyl) benzfuran
  • Preparation method of 2-alkyl -3-(4-hydroxybenzene formyl) benzfuran
  • Preparation method of 2-alkyl -3-(4-hydroxybenzene formyl) benzfuran

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Put 100g of 2-butyl-3-(4-methoxybenzoyl)benzofuran and 170ml of toluene into a three-necked flask, add 43g of aluminum trichloride, raise the temperature, keep the temperature at 105-120°C for 3 hours, then cool down Add 100ml of hydrochloric acid and 170ml of water to the feed solution at 50-60°C, heat and stir for 1 hour, let stand to separate layers, discard the water layer, and collect the organic layer.

[0032] Add 40ml of hydrochloric acid and 300ml of water to the feed solution, stir, let stand to separate the layers, and separate the water layer. After mixing 66g of sodium hydroxide and 400ml of water, add to the organic layer, stir, let stand to separate layers, collect the lye layer and put it into a three-necked flask. Add dilute hydrochloric acid dropwise to the feed solution to adjust the pH to 2, stir, precipitate, filter, wash with water until neutral, and drain to obtain 2-butyl-3-(4-hydroxybenzoyl)benzofuran. The rate is 90.2%. By HPLC analysis, the ...

Embodiment 2

[0034] Put 8092-butyl-3-(4-methoxybenzoyl)benzofuran and 270ml of toluene into a three-necked flask, stir and heat, add 173g of anhydrous aluminum trichloride, heat up to 105-120°C and keep warm for reaction 3 hour, lower the temperature to 50-60°C, add 130ml of hydrochloric acid and 220ml of water to the feed solution, keep stirring for 1 hour, let stand to separate layers, discard the water layer, and collect the organic layer.

[0035] Add 50ml of hydrochloric acid and 375ml of water to the feed solution, stir, let stand to separate layers, and separate the water layer. After mixing 80g of sodium hydroxide and 480ml of water, add to the organic layer, stir, let stand to separate layers, collect the lye layer and put it into a three-necked flask. Add dilute hydrochloric acid dropwise to the feed solution to adjust the pH to 2, stir, precipitate, filter, wash with water until neutral, and drain to obtain 2-butyl-3-(4-hydroxybenzoyl)benzofuran. The yield was 89.0%. By HPLC a...

Embodiment 3

[0037] Put 509 2-butyl-3-(4-methoxybenzoyl)benzofuran and 340ml of toluene into a three-necked flask, add 210g of anhydrous aluminum trichloride, raise the temperature to 105-120°C, and keep the reaction for 3 hours. Cool down to 50-60°C, add 100ml of hydrochloric acid and 170ml of water to the feed solution, keep stirring for 1 hour, let stand to separate layers, discard the water layer, and collect the organic layer.

[0038] Add 40ml of hydrochloric acid and 300ml of water to the feed solution, stir, let stand to separate the layers, and separate the water layer. After mixing 64g of sodium hydroxide and 400ml of water, add to the organic layer, stir, let stand to separate layers, collect the lye layer and put it into a three-necked flask. Add dilute hydrochloric acid dropwise to the feed solution to adjust the pH to 2, stir, precipitate, filter, wash with water until neutral, and drain to obtain 2-butyl-3-(4-hydroxybenzoyl)benzofuran. The rate is 88.6%. The purity was 99....

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Abstract

The invention relates to a method for the preparation of 2-alkyl -3-(4-hydroxybenzene formyl) benzfuran, which refers to the field of pharmaceutical chemical technology. The invention dealkylates 2 - alkyl -3- (4-alkoxy benzoyl) benzfuran of raw material formula (II) in an organic solvent, in the presence of a Lewis acid catalyst , at the temperature between 100 DEG C and 175 DEG C, and then prepares the product of formula (I) by the steps of acid hydrolysis reaction, acid washing , alkali treatment and separation. The invention has the advantages of short reaction time, high yield and high product purity.

Description

technical field [0001] The invention relates to the technical field of medicine and chemical industry, in particular to a method for preparing 2-alkyl-3-(4-hydroxybenzoyl)benzofuran. Background technique [0002] 2-Alkyl-3-(4-hydroxybenzoyl)benzofuran is an intermediate for the preparation of antiarrhythmic drugs, especially 2-butyl-3-(4-hydroxybenzoyl)benzofuran is the preparation The necessary intermediate of the antiarrhythmic drug amiodarone hydrochloride. Its structure is as follows: [0003] [0004] wherein R represents a linear or branched alkyl group containing 1-5 carbon atoms. [0005] It is prepared by dealkylation reaction of 2-alkyl-3-(4-alkoxybenzoyl)benzofuran having the structure of formula (II). [0006] [0007] Wherein R1 represents a linear or branched alkoxy group of 1-5 carbon atoms, and R is as defined above; [0008] In the ZL200480038285.2 patent, 2-alkyl-3-(4-alkoxybenzoyl)-5-nitrobenzofuran is used in the presence of Lewis acid at a heat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/80
Inventor 刘桂云于辉
Owner DEZHOU UNIV