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Chemical preparation method of compound 2-methyl-5,7-dihydroxy chromone

A technology of dihydroxychromone and compound is applied in the field of synthesis of chromone compound, which can solve the problems of easy generation of by-products and high cost of production raw materials, and achieves the effects of low cost, high cost and easy cost.

Active Publication Date: 2014-12-24
GUANGDONG SYNYOO NEW MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

From the perspective of the synthetic route, the production raw material cost of this method is relatively high, by-products are easily produced during the synthetic process, and there are uncertain factors

Method used

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  • Chemical preparation method of compound 2-methyl-5,7-dihydroxy chromone
  • Chemical preparation method of compound 2-methyl-5,7-dihydroxy chromone
  • Chemical preparation method of compound 2-methyl-5,7-dihydroxy chromone

Examples

Experimental program
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Effect test

Embodiment 1

[0053] "One-pot reaction" for the preparation of 2-methyl-3-acetyl-5,7-diacetoxychromone

[0054] (1) Acylation-cyclization:

[0055] Phloroglucinol raw material (12.6 g, 0.1 mol) was added into a 1 L three-necked flask, and 100 mL of dichloromethane was added to dissolve it. Under the condition of stirring at -15°C, anhydrous aluminum trichloride (16g, 0.12mol) catalyst was added, and acetyl chloride (8.6g, 0.11mol) was added dropwise. After the dropwise addition was completed, the reaction was stirred at room temperature for 3 hours. After the reaction was monitored by TLC and the reaction was complete, that is, after the raw material phloroglucinol was completely consumed and converted, anhydrous sodium acetate (28.7g, 0.35mol) was added to the reaction solution; and acetyl chloride (78g, 1.0mol) was added dropwise, The dropwise addition was completed within half an hour. The temperature was raised to reflux, and the reaction was stirred for 2 hours. After the reaction w...

Embodiment 2

[0064] "One-pot reaction" for the preparation of 2-methyl-3-acetyl-5,7-diacetoxychromone

[0065] (2) Acylation-cyclization:

[0066] Add phloroglucinol raw material (12.6 g, 0.1 mol) into a 1 L three-necked flask, and add 100 mL of 1,2-dichloroethane to dissolve it. At a temperature of 0°C and stirring, anhydrous aluminum trichloride (14 g, 0.105 mol) was added as a catalyst, and acetyl chloride (7.8 g, 0.1 mol) was added dropwise. After the addition was complete, the reaction was stirred at room temperature for 2 hours. After the reaction is monitored by TLC and the reaction is complete, that is, after the raw material phloroglucinol is completely consumed and converted, anhydrous sodium acetate (16.4g, 0.2mol) is added to the reaction solution; and acetyl chloride (63g, 0.8mol) is added dropwise, The dropwise addition was completed within half an hour. The temperature was raised to reflux, and the reaction was stirred for 1 hour. After the reaction, excess acetyl chlorid...

Embodiment 3

[0073] "One-pot reaction" for the preparation of 2-methyl-3-acetyl-5,7-diacetoxychromone

[0074] (1) Acylation-cyclization:

[0075] Add phloroglucinol raw material (12.6 g, 0.1 mol) into a 1 L three-necked flask, and add 100 mL of 1,2-dichloroethane to dissolve it. Under stirring conditions at a temperature of 10°C, anhydrous aluminum trichloride (16 g, 0.12 mol) was added as a catalyst, and acetyl chloride (9.4 g, 0.12 mol) was added dropwise. After the dropwise addition was completed, the reaction was stirred at room temperature for 5 hours. After the reaction was monitored by TLC and the reaction was complete, that is, after the raw material phloroglucinol was completely consumed and converted, anhydrous sodium acetate (41g, 0.5mol) was added to the reaction solution; and acetyl chloride (94g, 1.2mol) was added dropwise, and then The dropwise addition was completed within half an hour. The temperature was raised to reflux, and the reaction was stirred for 4 hours. Afte...

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Abstract

The invention provides a chemical preparation method of a compound 2-methyl-5,7-dihydroxy chromone. The chemical preparation method comprises the following steps: by mainly adopting phloroglucinol and acetyl chloride as raw materials, firstly synthesizing 2,4,6-trihydroxy acetophenone by using Lewis acid as a catalyst in an organic solvent system; then replenishing acetyl chloride and a condensation catalyst namely anhydrous sodium acetate, further performing condensation with generated 2,4,6-trihydroxy acetophenone, and performing 'one-pot reaction' to obtain 2-methyl-3-acetyl-5,7-diacetoxyl chromone; and finally, removing acetyl and acetoxyl of 2-methyl-3-acetyl-5,7-diacetoxyl chromone by virtue of soda boiling to obtain a target product namely 2-methyl-5,7-dihydroxy chromone. The method provided by the invention is simple and easily-available in adopted raw material, can simplify the reaction steps, and has the advantages of low cost, high yield, mild reaction condition, applicability in industrial production, environmental protection and the like.

Description

technical field [0001] The invention relates to a synthesis method of a chromone compound, which belongs to the field of chemical industry, in particular to a chemical preparation method of the compound 2-methyl-5,7-dihydroxychromone. Background technique [0002] 2-Methyl-5,7-dihydroxychromone is an important organic compound, which has anti-wrinkle, anti-oxidation and other skin anti-aging effects, and is widely used in the field of cosmetics. Generally speaking, human skin is very vulnerable to damage due to direct contact with the external environment and being stimulated by various environmental factors such as oxidation, drying and ultraviolet rays. At the same time, due to the influence of internal factors such as age, diet and living habits, skin function declines and genetic abnormalities lead to aging of the skin. [0003] 2-Methyl-5,7-dihydroxychromone, as a compound that can be used as an anti-wrinkle component, has been described in many patents related to cosm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/22
CPCC07D311/22
Inventor 史华红宋继国梁东冯中旺陈少渠麻勇刚
Owner GUANGDONG SYNYOO NEW MATERIAL
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