Method for synthesizing veratric acid

A synthesis method and technology of veratrol are applied in chemical instruments and methods, preparation of carboxylate, preparation of organic compounds, etc., can solve the problems of consumption of potassium tert-butoxide, high price of veratrol, etc., and achieve a short production cycle. , the effect of reducing costs and reducing environmental pollution

Inactive Publication Date: 2007-12-26
ZHEJIANG UNIV
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  • Abstract
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Problems solved by technology

The main disadvantage of this method is to consume a large amount of expensive potassium tert-butoxide, and the raw material veratrol is expensive

Method used

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  • Method for synthesizing veratric acid
  • Method for synthesizing veratric acid
  • Method for synthesizing veratric acid

Examples

Experimental program
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Effect test

Embodiment 1

[0018] (1) Preparation of Veratrate:

[0019] In the flask equipped with stirring, condenser and thermometer, add veratraldehyde (33.2g, 0.20mol), calcium hydroxide (74g, 1.0mol), isopropanol aqueous solution (250mL, water content is 10% (v) ), formalin solution (45.0g, 35%wt), and reacted for 2.5h at a temperature of about 50°C. Filtration yielded a yellow solid, veratrate.

[0020] (2) Preparation of veratrol product:

[0021] At room temperature, sulfuric acid aqueous solution (20%wt) was added dropwise to veratrate for 0.5h, and the pH at the end point of acidification was 4. After filtering, washing and drying, 16.32 g of a light yellow solid was obtained, which was a veratronic acid product, and the yield was 88.5%.

[0022] The measurement results of the physical properties of the veralic acid product: a light yellow solid with a melting point of 177-178°C, which is consistent with the value in the literature (Phytochemistry, 1990, 29(3), 1014-1016).

[0023] Gas ch...

Embodiment 2

[0026] In the flask equipped with stirring, condenser and thermometer, add veratraldehyde (63.1g, 0.38mol), sodium carbonate (60.4g, 0.57mol), n-butanol aqueous solution (550mL, water content is 15% (v) ), formalin solution (60.0g, 35%wt), and reacted for 1.5h at a temperature of about 50°C. A yellow solid was obtained as veratrate. At room temperature, sulfuric acid aqueous solution (30%wt) was added dropwise to the veratrate for 2 hours, and the pH at the end point of the acidification was 2. 28.95 g of the product was obtained, and the yield was 82.6%.

Embodiment 3

[0028] In the flask equipped with stirring, condenser and thermometer, add veratraldehyde (107.9g, 0.65mol), potassium hydroxide (218.4g, 3.9mol), aqueous ethanol (700mL, water content is 25% (v)) , Paraformaldehyde (97.5g, 3.25mol), reacted at a temperature of about 100°C for 4h. A yellow solid was obtained as veratrate. At room temperature, nitric acid aqueous solution (5%wt) was added dropwise to veratrate for 1.5h, and the pH at the end point of acidification was 3. 56.16 g of the product was obtained with a yield of 93.7%.

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Abstract

This invention relates to a method for synthesizing organic compound, more specifically, veratric acid. The method comprises: performing disproportionation salification reaction on veratraldehyde with aldehyde and alkali in alcohol/water solvent, and acidifying to obtain veratric acid. The method acoids the utilization of 1, 3-dinitrobenzene and potassium butoxide, and has such advantages as little environmental pollution, high productivity and short production cycle.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing veratronic acid. Background technique [0002] Veratronic acid (3,4-dimethoxybenzoic acid) with structural formula as shown in S-1 is a commonly used intermediate in chemical synthesis, widely used in industry, medicine, agriculture and other fields, and is the synthetic drug albino hydrochloride Key intermediates of compounds such as fuzosin (structural formula shown in Figure S-2). [0003] [0004] The synthetic method of veratrol is less seen in the report, and main method commonly used at present is as document (TetrahedronLetters, 2002,43 (28), 4985-4987) report, in organic solvent tert-butyl alcohol, take veratrol as raw material, add 1,3-Dinitrobenzene and potassium tert-butoxide, oxygen as an oxidant, synthesize the target product. The main disadvantage of this method is to consume a large amount of expensive potassium tert-but...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C65/21C07C51/00
Inventor 陈新志沙兰兰
Owner ZHEJIANG UNIV
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