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Method for preparing 2, 3, 4-trimethoxybenzaldehyde

A technology of trimethoxybenzaldehyde and trimethoxybenzene, applied in the field of medicine and chemical industry, can solve the problems of unfavorable industrialized production, high price and high production cost, and achieve the effects of low market price, low cost, good yield and purity

Inactive Publication Date: 2013-01-16
CHANGZHOU HUANAN CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the price of raw material 2,3,4-trihydroxybenzaldehyde and phase transfer catalyst used in this method is relatively high, resulting in high production cost, which is not conducive to industrial production.

Method used

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  • Method for preparing 2, 3, 4-trimethoxybenzaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] In a three-neck flask equipped with a thermometer, stirred and cooled by a water bath, add 100 g of raw materials pyrogallic acid and 200 g of water, stir until dissolved, add 330 g of dimethyl sulfate and 400 g of 30% sodium hydroxide dropwise at room temperature, and after the addition is complete, the reactor Keep the temperature at 30°C for 30 minutes. Stand to separate and separate, and wash the upper organic layer with water until neutral to obtain 120g of intermediate 1,2,3-trimethoxybenzene with a yield of 90%

[0020] Add 120g of the above-mentioned intermediate 1,2,3-trimethoxybenzene and 120g of DMF to a three-neck flask equipped with a thermometer, stirring and heating jacket, add 240g of phosphorus oxychloride dropwise, and raise the temperature to 70-80°C for 10 hour, cooled and poured the reaction solution into 500g ice water for hydrolysis, extracted three times with 300ml ethyl acetate, recovered ethyl acetate under reduced pressure, collected the disti...

Embodiment 2

[0022] In a three-neck flask equipped with a thermometer, stirred and cooled by a water bath, add 100 g of raw materials pyrogallic acid and 200 g of water, stir until dissolved, add 365 g of dimethyl sulfate and 400 g of 30% sodium hydroxide dropwise at room temperature, and after the addition is complete, the reactor Keep the temperature at 45°C for 30 minutes. After static separation, the upper organic layer was washed with water to neutrality to obtain 123g of intermediate 1,2,3-trimethoxybenzene with a yield of 92.5%

[0023] Add 123g of the above-mentioned intermediate 1,2,3-trimethoxybenzene and 123g of DMF to a three-neck flask with a thermometer, stirring and heating jacket, add 246g of phosphorus oxychloride dropwise, and heat up to 70-80°C for 10 hour, cooling and pouring the reaction solution into 500g ice water for hydrolysis, extracting three times with 300ml ethyl acetate, recovering ethyl acetate under reduced pressure, collecting the distillate by distillation...

Embodiment 3

[0025] In a three-neck flask equipped with a thermometer, stirred and cooled by a water bath, add 100 g of raw materials pyrogallic acid and 200 g of water, stir until dissolved, add 400 g of dimethyl sulfate and 400 g of 30% sodium hydroxide dropwise at room temperature, and after the addition is complete, the reactor Keep the temperature at 60°C for 30 minutes. After static separation, the upper organic layer was washed with water to neutrality to obtain 123g of intermediate 1,2,3-trimethoxybenzene with a yield of 92.5%

[0026] Add 123g of the above-mentioned intermediate 1,2,3-trimethoxybenzene and 123g of DMF to a three-neck flask with a thermometer, stirring and heating jacket, add 246g of phosphorus oxychloride dropwise, and heat up to 70-80°C for 10 hour, cooling and pouring the reaction solution into 500g ice water for hydrolysis, extracting three times with 300ml ethyl acetate, reclaiming ethyl acetate under reduced pressure, collecting the distillate by distillation...

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Abstract

The invention relates to a method for preparing 2, 3, 4-trimethoxybenzaldehyde which is a medical intermediate. The method includes that a coking gallic acid is utilized as a raw material, dimethyl sulfate is utilized as an alkylate reagent, under the condition of existence of sodium hydroxide, methylation is performed through an O-alkylation reaction to obtain an intermediate 1, 2, 3-trimethoxybenzene, and the 1 ,2, 3-trimethoxybenzene and a Vilsmeier-Haack reagent are subjected to a formylation reaction to obtain the 2, 3, 4-trimethoxybenzaldehyde. The method for preparing the 2, 3, 4-trimethoxybenzaldehyde has the advantages that the product purity is above 99%, the total yield reaches to 73%, raw materials are easy to obtain, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and in particular relates to a preparation method of compound 2,3,4-trimethoxybenzaldehyde as a medicine intermediate. Background technique [0002] 2,3,4-Trimethoxybenzaldehyde is a white crystalline powder with the chemical formula C 10 h 12 o 4 , with a molecular weight of 196.2 and a melting point of 38-40 degrees, is an important pharmaceutical intermediate, mainly used in new drugs Ca 2+ Synthesis of channel blockers. The drug can be selectively used in cerebral arteries to reduce the incidence of headaches, and is mainly used to prepare the intermediate of trimetazidine. [0003] The application number is 200310112817.X, and the Chinese patent literature with the publication number CN1556086A discloses a preparation method of 2,3,4-trimethoxybenzaldehyde, using gallic acid derivative 2,3,4-trihydroxybenzaldehyde as The main raw material is dimethyl sulfate as an alkylatin...

Claims

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Application Information

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IPC IPC(8): C07C47/575C07C45/45
Inventor 王六五魏巍魏晓廷王锁海
Owner CHANGZHOU HUANAN CHEM
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