Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for synthesizing 2,4,5-trimethoxyethylphenylketone intermediate of alpha-asarin

A technology of trimethoxybenzene and intermediates, which is applied in the field of the key intermediate 2 of the synthetic drug a-asarone, which can solve the problems of toxic organic solvents and cumbersome acetone operations, and achieve low cost, good product quality and safe operation reliable effect

Inactive Publication Date: 2010-11-24
广西中医学院
View PDF2 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The purpose of the present invention is to provide a kind of 1,2,4-trimethoxybenzene as raw material, after adding solvent, directly react with propionic acid or propionic anhydride, propionylation reaction, hydrolysis reaction to synthesize 2,4,5-trimethoxybenzene A convenient method for propiophenone, which can solve the problems of cumbersome operation, use of toxic organic solvents, etc.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for synthesizing 2,4,5-trimethoxyethylphenylketone intermediate of alpha-asarin
  • Method for synthesizing 2,4,5-trimethoxyethylphenylketone intermediate of alpha-asarin
  • Method for synthesizing 2,4,5-trimethoxyethylphenylketone intermediate of alpha-asarin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Add 33.6 grams of 1,2,4-trimethoxybenzene and 25 grams of propionic acid, 400 grams of polyphosphoric acid (PPA) in a dry reactor, and stir the reaction at 45 ± 5 ° C, and detect the end point of the reaction with TLC (expansion system : n-hexane / ethyl acetate=8 / 2, concentrated sulfuric acid for color development), it takes about 5 hours to react, after the reaction is completed, cool to room temperature, pour the reactant into ice water, stir, and a large amount of solids are precipitated. For the amount of ice water, the mixed volume of ice and water is about 15-20 ml for every 10 grams of PPA used, or the mixed volume of ice and water is about 15-20 ml for every 10 grams of solvent used. Filter, wash with water until neutral, recrystallize with methanol, and dry to obtain 40.5 g of off-white solid, yield 90.4% (based on 1,2,4-trimethoxybenzene), mp 106-108°C.

Embodiment 2

[0037] Add 19.5 milliliters of 85% phosphoric acid and 30.6 grams of phosphoric anhydride into the dry reaction bottle and heat on a water bath until the phosphoric anhydride is completely dissolved, about 2 to 3 hours. Cool to room temperature, then add 1.4 grams of propionic acid, 1.68 grams of 1,2,4-trimethoxybenzene and 0.2 grams of sodium polyphosphate as an auxiliary agent, stir the reaction at 55±5°C, use TLC to detect the end of the reaction, and react for about 4 hours After the reaction is completed, cool to room temperature, pour the reactant into ice water, stir, and a large amount of solid precipitates out. Filter, wash with water until neutral, recrystallize with methanol, and dry to obtain 1.9 g of off-white product. Yield 84.8%, mp 106-108°C.

Embodiment 3

[0039] Add 5.04 grams of 1,2,4-trimethoxybenzene, 3 grams of propionic acid, 70 grams of polyphosphoric acid and 0.4 grams of auxiliary potassium dihydrogen phosphate into the dry reaction flask, and stir the reaction at 85±5°C. The end point of the reaction was detected by TLC. After the reaction was completed for about 3 hours, the reaction was cooled to room temperature, and the reactant was poured into ice water, stirred, and a large amount of solids were precipitated. Filter, wash with water until neutral, recrystallize with methanol, and dry to obtain 6 g of off-white solid product with a yield of 89.3%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for synthesizing a 2,4,5-trimethoxyethylphenylketone intermediate of alpha-asarin, which is characterized by comprising the following steps of: directly reacting 2,4,5-trimethoxybenzene, which servers as a raw material, with propanoic acid or propionic anhydride under the action of polyphosphoric acid, or a mixture of phosphoric acid and phosphoric anhydride, or a mixture of the polyphosphoric acid, the phosphoric acid and the phosphoric anhydride; and performing hydrolysis to obtain the 2,4,5-trimethoxyethylphenylketone. The product can be used as the raw material or the intermediate of the alpha-asarin or the raw material for synthesizing other medicaments, and also can be used as spices. The method of the invention has the advantages of simple process, low cost, high product quality, high yield and the like and is safe and reliable in operation and suitable for industrial production. The method can effectively solve the problems of complicated operation and the like of the synthesis of the 2,4,5-trimethoxyethylphenylketone intermediate of the alpha-asarin.

Description

technical field [0001] The invention relates to a convenient method for synthesizing 2,4,5-trimethoxypropiophenone, a key intermediate of drug α-asarone. Background technique [0002] 2,4,5-Trimethoxypropiophenone is a chemical component present in Piper marginatum. It is an important raw material and intermediate for the synthesis of expectorant and antiasthmatic drug a-asarone, and it can also be used as a spice . [0003] Indian Patent Indian Pat.Appl., 2003 DE 00119, 16 Mar 2007 and Chinese Invention Patent CN 101492351, and Zhang Ling and Liu Suyun in "Preparation of α-Asarone", "Chinese Journal of Pharmaceutical Industry", 2007, 38(7) : 477-478, all proposed to use 1,2,4-trimethoxybenzene as raw material, anhydrous aluminum trichloride or anhydrous zinc chloride as catalyst, and carry out propionylation reaction to synthesize 2,4,5 through propionyl chloride - Trimethoxypropiophenone. The disadvantage of this method is that there are many side reactions, a large amo...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/84C07C45/46
Inventor 陈毅平
Owner 广西中医学院
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com