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Method for synthesizing veratraldehyde

A technology of veratraldehyde and its mixture, which is applied in the field of synthesizing veratraldehyde, can solve the problems of difficult popularization and application, high cost, high price of vanillin, etc., achieve good economic and social value, reduce cost, and shorten the process route

Inactive Publication Date: 2011-05-25
四川鸿康药物化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] This method is a relatively classic synthetic method. The raw materials using this synthetic process route are easy to obtain, simple to operate, high in yield, and easy to industrialized production. However, the price of vanillin is relatively expensive and the cost is high, so it is not easy to promote and apply in the market.

Method used

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  • Method for synthesizing veratraldehyde
  • Method for synthesizing veratraldehyde
  • Method for synthesizing veratraldehyde

Examples

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Effect test

Embodiment 1

[0029] A method for synthesizing veratraldehyde, characterized in that: using catechol as raw material, undergoing methylation reaction and formylation reaction successively, catechol generates veratraldehyde after the above-mentioned two-step reaction; wherein:

[0030] (1) Catechol synthesis of veratrole: add catechol 1100g in 5000mL reactor A, dissolve catechol with toluene solvent, add dimethyl sulfate 2400g to catechol, heat The mixture formed by catechol and dimethyl sulfate, the initial temperature is controlled at 20-40°C, 11.0g methylation catalyst benzyltriethylammonium chloride (TEBAC) is dissolved with 1200mL liquid caustic soda (30%wt) , metered and dropped 830mL of the above mixed solution under the condition of stirring, and controlled the rate of addition to complete the dropwise addition within 5 hours. During the dropping process, the temperature of the reaction solution was controlled at 35-40°C, and continued to stir for 30min after the dropwise addition; ca...

Embodiment 2

[0035] A method for synthesizing veratraldehyde, characterized in that: using catechol as raw material, undergoing methylation reaction and formylation reaction successively, catechol generates veratraldehyde after the above-mentioned two-step reaction; wherein:

[0036](1) Catechol synthesis of veratrole: add catechol 1100g in 5000mL reactor A, dissolve catechol with toluene solvent, add dimethyl sulfate 2400g to catechol, heat The mixture formed by catechol and dimethyl sulfate, the initial temperature is controlled at 20-40°C, the methylation catalyst is benzyltriethylammonium chloride (TEBAC) 2.2g, tetramethylammonium hydroxide (TMAH) 8.8g was dissolved with 1200mL liquid caustic soda (30%wt), and 830mL of the above-mentioned mixed solution was metered and dropped under stirring conditions, and the dropping rate was controlled to finish adding in 5 hours. During the dropping process, the temperature of the reaction solution was controlled at 35-40°C, Continue to stir for 3...

Embodiment 3

[0039] A method for synthesizing veratraldehyde, using catechol as raw material, successively undergoes methylation reaction and formylation reaction, and catechol generates veratraldehyde after the above-mentioned two-step reaction; wherein:

[0040] (1) pyrocatechol is synthesized veratrole: in 6300L reactor A, add pyrocatechol 1100Kg, at least one solvent 200kg in toluene, butyl acetate, acetone is wetting and dissolving pyrocatechol; Add Dimethyl sulfate 2018kg, be stirred into slurry; Tetramethylammonium hydroxide (TMAH) 10kg, dissolve with 3500L liquid caustic soda (30%wt), measure and drop above-mentioned mixed solution 1500L under stirring condition, control drop rate in 5 hours After the dropwise addition, control the temperature of the reaction solution at 20-40°C, and continue to stir for 30 minutes after the dropwise addition; under the action of the catalyst, catechol and methylating reagent are partially converted into guaiacol; To 70°C, continue to drop the rema...

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Abstract

The invention discloses a method for synthesizing veratraldehyde. In the method, a methylation reaction and a formylation reaction are performed on catechol serving as a raw material in turn to generate the veratraldehyde, wherein the methylation reaction comprises two reaction stages: guaiacol is mainly generated at the first reaction stage, and the veratrole is generated at the second reaction stage; and during the formylation reaction, the veratrole and a formylation reagent are synthesized to obtain the veratraldehyde. Through comprehensive utilization of a methylation reagent and the formylation reagent, the current situation that the veratraldehyde can only be synthesized by expensive vanillin in the conventional industrial production is changed, the process route for synthesizing the veratraldehyde is effectively shortened, and the cost of a product is reduced; both the yield and the content of the veratraldehyde prepared by the method are greater than those of the veratraldehyde prepared in the prior art; due to the increase of the yield and the content of the veratraldehyde, the process for synthesizing the veratraldehyde is effectively controlled; thus the entire process flow is smooth and stable.

Description

technical field [0001] The invention relates to a method for synthesizing veratraldehyde by using catechol as raw material. Background technique [0002] Veratraldehyde (Veratraldehyde), also known as methyl vanillin, methyl vanillin, chemical name: 3,4-dimethoxybenzaldehyde, molecular formula C 9 h 10 o 3 , is a kind of synthetic fragrance with vanillabeans (Vanillabeans) type fragrance, and it is also a pharmaceutical intermediate with many uses. It is not only an important intermediate in the synthesis of dopa drugs, such as levodopa L-DOPA, but also can be used to synthesize the anti-allergic drug Tranicob, the antihypertensive drug prazosin and tetrahydropalmatate for the treatment of arthritis. The heart-selective adrenaline β-receptor blocker veratramine is used to prevent and treat allergic asthma and allergic rhinitis, and it can also be used to synthesize some important pharmaceutical intermediates such as 6, 7-dimethoxy-2-styrene quinoline, 6,7-dimethoxy-2,4-d...

Claims

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Application Information

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IPC IPC(8): C07C47/575C07C45/54
CPCY02P20/582
Inventor 杜廷军毛逢银唐云段向阳
Owner 四川鸿康药物化学有限公司
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