Method for synthesizing asarin

A synthetic method and the technology of asarone, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of unfavorable industrial production and low yield, and achieve low production cost, simple process, and easy industrialization Effect

Active Publication Date: 2007-12-26
广西两面针亿康药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There have been many reports on the synthesis of α-asarone, but the yields of various methods are relatively low, which is not conducive to industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Put the adduct generated by 7592,4,5-trimethoxybenzaldehyde on a rotary evaporator, recover THF at 46°C, cool to room temperature, add 375mL ethyl acetate, stir at 22°C for 5h, add Stir 75ml of acetic anhydride for 60min, then add 350ml of distilled water and stir rapidly for 10s, separate the water layer, wash the ester layer with sodium carbonate solution to pH=9~10, then wash with saturated saline, dry over anhydrous sodium sulfate, filter, and concentrate , then add 15mL of 70% ethanol to shake well, cool to room temperature, add a small amount of seed crystals, put it in the freezing layer of the refrigerator overnight, filter, then transfer the solid to a 250mL dry single-necked flask, add 25mL of 80% ethanol to heat to dissolve, and crystallize at room temperature, It was filtered, dried for 5 hours (vacuum at 46° C.), weighed 48.8 grams, and the yield was 61.31%. (GC-MS detection content is 99.21%)

Embodiment 2

[0017] Put the adduct formed by 7592,4,5-trimethoxybenzaldehyde on a rotary evaporator, recover THF at 46°C, cool to room temperature, add 1500mL ethyl acetate, and stir at 35°C for 3.5h, Add 84ml of acetic anhydride and stir for 50min, then add 350ml of distilled water and stir rapidly for 10s, remove the water layer, wash the ester layer with sodium carbonate solution to PH=9~10, then wash with saturated saline, dry over anhydrous sodium sulfate overnight, filter, Concentrate, then add 26mL of 65% ethanol to shake well, cool to room temperature, add a small amount of seed crystals, put in the freezing layer of the refrigerator overnight, filter, then transfer the solid to a 250mL dry single-necked flask, add 25mL of 85% ethanol to heat to dissolve, and crystallize at room temperature , filtered, dried for 5h (vacuum 46°C), weighed 48.5 grams, and the yield was 60.94%. (GC-MS detection content is 99.78%)

Embodiment 3

[0019] Put the adduct formed by 12592,4,5-trimethoxybenzaldehyde on a rotary evaporator, recover THF at 46°C, cool to room temperature, add 2500mL ethyl acetate, and stir at 15°C for 3.5h, Add 187.5ml of acetic anhydride and stir for 30min, then add 350ml of distilled water and stir rapidly for 10s, remove the water layer, wash the ester layer with sodium carbonate solution to pH=9~10, then wash with saturated saline, dry overnight with anhydrous sodium sulfate, and filter , Molecular distillation to recover ethyl acetate, then add 30mL of 70% ethanol to shake well, cool to room temperature, add a small amount of seed crystals, put in the freezing layer of the refrigerator overnight, filter, then transfer the solid to a 250mL dry single-necked flask, add 40mL80% Ethanol was heated to dissolve, crystallized at room temperature, filtered, dried for 5 hours (vacuum 46° C.), weighed 86.22 grams, and the yield was 65%. (GC-MS detection content is 100%)

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Abstract

This invention relates to a method for synthesizing alpha-asarone. The eliminating reagents are ethyl acetate and acetic anhydride. The weight/volume ratio of 2,4,5-trimethoxybenzaldehyde to ethyl acetate is 1:(5-50), and that of 2,4,5-trimethoxybenzaldehyde to acetic anhydride is 1:(0.5-5). Organic acids are removed by sodium carbonate aqueous solution. Ethyl acetate is separated by molecular distillation. The alpha-asarone crystal is obtained by recrystallization. The method has such advantages as high product purity, simple process, low production cost, easy industrialization, and good product physicochemical properties. The alpha-asarone product can be directly added into medicines.

Description

technical field [0001] The invention belongs to a method for synthesizing α-asarone. Background technique [0002] α-Asarone mainly exists in the volatile oil of natural products such as calamus calamus and other plants. It has sedative, prolonged hypnotic and antibacterial effects. It is mostly used clinically for the treatment of chronic bronchitis, epilepsy, coma and other mental diseases. Since the 1960s, the extraction, synthesis, pharmacology, toxicology and clinical studies of the active ingredient α-asarone monomer of calamus plants have been extensively studied at home and abroad, and significant progress has been made. [0003] There have been many reports on the synthesis of α-asarone, but the yields of various methods are relatively low, which is not conducive to industrial production. Contents of the invention [0004] The technical problem to be solved by the present invention is to provide a method for synthesizing α-asarone with higher yield. [0005] The...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/205C07C41/30
Inventor 王立升韦泰新乔红运李源志冷承先
Owner 广西两面针亿康药业股份有限公司
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