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Method for synthesizing isoliquirtigenin

A technology of isoliquiritigenin and synthesis method, applied in the direction of condensation preparation of carbonyl compounds, separation/purification of carbonyl compounds, organic chemistry, etc., to achieve high yield, improve product purity, and simple method

Inactive Publication Date: 2009-01-28
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] So far, there are a few domestic and foreign reports on the synthesis method of isoliquiritigenin, but there is only one patent (Patent No. 200410065383)

Method used

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  • Method for synthesizing isoliquirtigenin
  • Method for synthesizing isoliquirtigenin
  • Method for synthesizing isoliquirtigenin

Examples

Experimental program
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Embodiment 1

[0037] Embodiment 1: A, under Lewis base catalysis, the synthesis of 2,4-dihydroxyacetophenone: in 100ml round-bottomed flask, add 18g fully dry resorcinol (place 30 hours under 120 ℃), glacial acetic acid 55ml , 20 g of molten sodium ethylate was refluxed for 1.5 hours with stirring. After the reactant was cooled to room temperature (25°C, the same below), it was poured into ice water and stirred continuously to precipitate crystals, filtered, washed 3 times with water, dried, and recrystallized from ethanol to obtain a yellow solid, namely 15g of 2,4-dihydroxyacetophenone . mp143-144°C (literature 142-144°C).

[0038] B. Synthesis of 2-hydroxyl-4-methoxyacetophenone: add 6.5g 2,4-dihydroxyacetophenone, potassium carbonate 60g and acetone 250ml to a 500ml round-bottomed flask, and add it dropwise quickly at room temperature 50ml Me diluted in acetone 2 SO 4 0.03mol, after the addition was completed, the reaction was continued for 3 hours, and potassium carbonate was filt...

Embodiment 2

[0042] Embodiment 2: A, under Lewis base catalysis, the synthesis of 2,4-dihydroxyacetophenone: in 100ml round bottom flask, add the resorcinol of 11g fully dry (place 24 hours under 120 ℃), 30ml glacial acetic acid , 15 g molten ZnCl 2 , stirring under reflux for 1 hour. After the reactant was cooled to room temperature (25°C, the same below), it was poured into ice water and stirred continuously to precipitate crystals, filtered, washed 5 times with water, dried, and recrystallized with 50% ethanol to obtain 9 g of a yellow solid, which was 2,4-dihydroxy Acetophenone. mp142-144°C (literature 142-144°C).

[0043] B, the synthesis of 2-hydroxyl-4-methoxyacetophenone: 4g 2,4-dihydroxyacetophenone, potassium carbonate 44.5g and acetone 200ml are added to a 500ml round-bottomed flask, which is used for rapid dropwise addition at room temperature 6ml of chloromethyl methyl ether diluted with 35ml of acetone was added, and the reaction was continued for 2 hours, and potassium ca...

Embodiment 3

[0047] Embodiment 3: A, under Lewis base catalysis, the synthesis of 2,4-dihydroxyacetophenone: in the 150ml round bottom flask, add 15g fully dry resorcinol (place 24 hours under 120 ℃), glacial acetic acid 50ml , molten NaH 10g, refluxed for 1.5 hours with stirring. After the reactant was cooled to room temperature (25°C, the same below), it was poured into ice water and stirred continuously to precipitate crystals, filtered, washed 4 times with water, dried, and recrystallized from 50% ethanol to obtain a yellow solid, namely 2,4-dihydroxyphenylethyl Ketones 12.5g. mp143-144°C (literature 142-144°C).

[0048] B, the synthesis of 2-hydroxyl-4-methoxyacetophenone: add 5.0g 2,4-dihydroxyacetophenone, potassium carbonate 55g and acetone 250ml to a 500ml round-bottomed flask, and add it dropwise quickly at room temperature 8ml of chloromethyl methyl ether diluted with 40ml of acetone was added, and the reaction was continued for 2 hours after the addition, and potassium carbon...

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Abstract

The invention discloses a synthetic method of a chemical substance isoliquiritigenin. The synthetic method comprises the steps as follows: A. 2,4-dihydroxyacetophenone is synthesized under the catalysis of Lewis base; B. 2-hydroxy-4-methoxyacetophenone is synthesized; C. 3-(4-hydroxyphenyl)-1-(4-methoxy-2-hydroxyphenyl)-acrylketone is synthesized and recrystallized; D. 3-(4-hydroxyphenyl)-1-(2,4-dihydroxyphenyl)-acrylketone, that is, the isoliquiritigenin, is synthesized and recrystallized; E. the crude products of the obtained isoliquiritigenin is eluted and refined by column chromatography to obtain the isoliquiritigenin product, and after the detections of ultra violet, infrared, mass spectrum and nuclear magnetic resonance, the isoliquiritigenin product has the same spectrogram with the isoliquiritigenin standard product. The synthetic method of the invention has the advantages of simple method, available raw materials, low price, higher yield, etc.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and more specifically relates to a synthesis method of isoliquiritigenin. Background technique [0002] Licorice was first recorded in "Shen Nong's Materia Medica", also known as Guolao ("Famous Doctors"). Traditional Chinese medicine records that licorice not only has the function of reconciling various medicines, but also detoxifies. Therefore, in ancient prescriptions, licorice appears frequently, and the more famous compound is Zhigancao Decoction ("Treatise on Febrile Diseases"). At present in Japan, glycyrrhizin preparation is recognized as a better drug for the treatment of chronic hepatitis, and is widely used in the treatment of acute and chronic hepatitis, severe hepatitis and liver cirrhosis. [0003] In recent decades, the value of active ingredients in licorice has attracted much attention from scholars at home and abroad, and research has progressed rapidly. Isoliquiriti...

Claims

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Application Information

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IPC IPC(8): C07C49/835C07C45/46C07C45/78
Inventor 杨静周敏君余伟程昊李颖叶岚岚张晶
Owner WUHAN UNIV
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