A kind of synthetic method of isoliquiritigenin

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 the effects of high yield, simple method and low price

Inactive Publication Date: 2012-02-01
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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  • A kind of synthetic method of isoliquiritigenin
  • A kind of synthetic method of isoliquiritigenin
  • A kind of synthetic method of isoliquiritigenin

Examples

Experimental program
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Embodiment 1

[0037] Example 1: A. Synthesis of 2,4-dihydroxyacetophenone catalyzed by Lewis base: In a 100ml round bottom flask, add 18g of fully dried resorcinol (placed at 120°C for 30 hours) and 55ml of glacial acetic acid , 20g of molten sodium ethoxide, reflux for 1.5 hours under stirring. After the reactant was cooled to room temperature (25°C, the same below), it was poured into ice water with constant stirring to precipitate crystals, filtered, washed with water 3 times, dried, and recrystallized from ethanol to obtain a yellow solid, namely 15g of 2,4-dihydroxyacetophenone . mp143~144℃ (reference 142~144℃).

[0038] B. Synthesis of 2-hydroxy-4-methoxyacetophenone: add 6.5g of 2,4-dihydroxyacetophenone, 60g of potassium carbonate and 250ml of acetone into a 500ml round bottom flask, and use 50ml for rapid drip at room temperature Me diluted in acetone 2 SO 4 0.03mol, after addition, continue to react for 3 hours, and filter out potassium carbonate. The filtrate was evaporated to dr...

Embodiment 2

[0042] Example 2: A. Synthesis of 2,4-dihydroxyacetophenone under Lewis base catalysis: In a 100ml round-bottomed flask, add 11g of fully dried (placed at 120°C for 24 hours) resorcinol and 30ml of glacial acetic acid , 15g molten ZnCl 2 Reflux for 1 hour under stirring. After the reactant was cooled to room temperature (25°C, the same below), it was poured into ice water with constant stirring to precipitate crystals, filtered, washed with water 5 times, dried, and recrystallized with 50% ethanol to obtain 9g of yellow solid, which is 2,4-dihydroxyl Acetophenone. mp142~144℃ (reference 142~144℃).

[0043] B. Synthesis of 2-hydroxy-4-methoxyacetophenone: Add 4g of 2,4-dihydroxyacetophenone, 44.5g of potassium carbonate and 200ml of acetone to a 500ml round bottom flask, and use 35ml for rapid drip at room temperature 6ml of chloromethyl methyl ether diluted with acetone, after the addition, continue to react for 2 hours, and filter out potassium carbonate. The filtrate was evap...

Embodiment 3

[0047] Example 3: A. Synthesis of 2,4-dihydroxyacetophenone catalyzed by Lewis base: 15g of fully dried resorcinol (placed at 120°C for 24 hours) and 50ml of glacial acetic acid were added to a 150ml round bottom flask , 10g of molten NaH, reflux for 1.5 hours under stirring. After the reactant was cooled to room temperature (25°C, the same below), it was poured into ice water with constant stirring to precipitate crystals, filtered, washed 4 times with water, dried, and recrystallized with 50% ethanol to obtain a yellow solid, namely 2,4-dihydroxystyrene Ketone 12.5g. mp143~144℃ (reference 142~144℃).

[0048] B. Synthesis of 2-hydroxy-4-methoxyacetophenone: add 5.0g of 2,4-dihydroxyacetophenone, 55g of potassium carbonate and 250ml of acetone to a 500ml round bottom flask, and use 40ml for rapid drip at room temperature 8ml of chloromethyl methyl ether diluted with acetone, continue to react for 2 hours after the addition is complete, and filter out potassium carbonate. The f...

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Abstract

The invention discloses a method for synthesizing chemical substance isoliquiritigenin. The steps are: A. synthesis of 2,4-dihydroxyacetophenone under the catalysis of Lewis base; B. 2-hydroxy-4-methoxyphenethyl Synthesis of ketone; C, Synthesis and recrystallization of 3-(4-hydroxyphenyl)-1-(4-methoxy-2-hydroxyphenyl)-propenone; D, 3-(4-hydroxyphenyl )-1-(2,4-dihydroxyphenyl)-propenone is the synthesis and recrystallization of isoliquiritigenin; E, the crude isoliquiritigenin obtained above is purified by column chromatography to obtain the isoliquiritigenin product, After ultraviolet, infrared, mass spectrometry and nuclear magnetic resonance detection, it is the same as the spectrogram of isoliquiritigenin standard. The invention has the characteristics of simple method, readily available raw materials, low price, high yield and the like.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis, and more specifically relates to a method for synthesizing isoliquiritin. Background technique [0002] Licorice was first published in "Shen Nong's Materia Medica", alias Guo Lao ("Famous Doctors"). Traditional Chinese medicine records that licorice has both the effect of reconciling various medicines and detoxification. Therefore, in ancient prescriptions, licorice appears frequently. The more famous compound is Zhigancao Decoction ("Treatise on Febrile Diseases"). At present, in Japan, glycyrrhizin preparations are recognized as better drugs for the treatment of chronic hepatitis, and are widely used in the treatment of acute and chronic hepatitis, severe hepatitis and cirrhosis. [0003] In recent decades, the value of licorice's active ingredients has attracted much attention from domestic and foreign scholars, and research has progressed rapidly. Isoliquiritin is a small molecular comp...

Claims

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Application Information

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