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Method for synthesizing veratric acid

A technology of veratruic acid and carboxylic acid, which is applied in the preparation of carboxylate, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of low yield and expensive raw material veratrolic acid, etc.

Inactive Publication Date: 2011-02-02
卫洁
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Problems solved by technology

The main disadvantage of this type of method is that the raw material veratrol is relatively expensive, and the reaction often has an indeterminate by-product veratraldehyde, and the yield is generally not very high.

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  • Method for synthesizing veratric acid

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Embodiment 1

[0008] (1) Oxidation process: In a four-necked flask equipped with a stirrer, a thermometer, a condenser tube (calcium chloride drying tube should be added at the top) and a constant pressure dropping funnel, add 1000 mL of acetonitrile in advance, and then gradually add 8.50 mL of silver nitrate. g (0.05mol), 3,4-dimethoxybenzaldehyde 83.09g (0.5mol), after mixing evenly, add 285mL (2.5mol) of 30% hydrogen peroxide dropwise, after the dropwise addition is completed, slowly dissolve the reaction solution Heating to 50° C., maintaining this temperature, and detecting the content of 3,4-dimethoxybenzaldehyde by thin-layer chromatography until it is not detected, this process takes about 2.1 hours. At this time, quench the reaction with cold 10% sodium thiosulfate, extract with dichloromethane, separate the liquids and take the organic phase, evaporate the solvent to obtain the crude product.

[0009] (2) Purification The crude product obtained in (1) was washed with saturated so...

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Abstract

The invention discloses a method for synthesizing veratric acid, which is characterized in that: in a reaction that aldehydes are selectively catalytically oxidized by silver nitrate to generate carboxylic acid, the aldehydes are catalytically oxidized to generate the carboxylic acid under the catalysis of the silver nitrate and the oxidation of hydrogen peroxide. The technical scheme comprises the following steps of: (1) performing the oxidation process: dissolving 3,4-dimethoxybenzaldehyde in acetonitrile, adding a catalyst silver nitrate in an amount which is one tenth weight of the 3,4-dimethoxybenzaldehyde, dripping an oxidant hydrogen peroxide in an amount which is ten times weight of the 3,4-dimethoxybenzaldehyde, reacting at 50 DEG C for 2.1 hours, quenching the reaction by using sodium thiosulfate, and extracting by using dichloromethane; and (2) washing a product obtained in the step (1) by using saturated sodium bicarbonate, adjusting the pH of a water layer to be 5-6 by using hydrochloric acid, extracting by using dichloromethane, vaporizing the solvent to obtain the veratric acid. The hydrogen peroxide is a cheap and readily-available oxidant, and the silver nitrate is taken as the catalyst, so the reaction efficiency is effectively improved.

Description

technical field [0001] The invention relates to a reaction in which silver nitrate selectively catalyzes the oxidation of aldehydes to generate carboxylic acids. The aldehydes are catalyzed by silver nitrate and hydrogen peroxide is used as a catalyst to prepare carboxylic acids through catalytic oxidation, which belongs to the technical field of organic synthesis. Background technique [0002] It is extracted from the seeds of Trollius chi-nenisi Baill., Zygadenus, Veratrum and Schoeno-caulon offricinale. Veratronic acid containing one molecule of water of crystallization is an odorless crystal. It loses water at 100°C. The melting point is 180-181°C. If rhombohedral crystals will sublimate. Soluble in ethanol, ether. Almost insoluble in cold water, slightly soluble in boiling water, mainly used as chemical reagents. Veratronic acid is a commonly used chemical synthesis intermediate, widely used in industry, medicine, pesticides and other fields, and is a key intermedi...

Claims

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Application Information

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IPC IPC(8): C07C65/21C07C51/285
Inventor 卫洁
Owner 卫洁
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