Method for synthesizing 5,7-dihydroxy flavone

A technology of dihydroxyflavone and a synthesis method, which is applied in the field of fine chemical drug synthesis, can solve the problems of not being developed into industrialized production, harsh equipment requirements, and high cost, and achieve the effects of shortening production time, low production cost, and low environmental pollution.

Inactive Publication Date: 2011-07-20
SHAANXI JIAHE PHYTOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] To sum up, the current existing methods for the preparation of chrysin are limited to the laboratory stage, with high costs, long routes, and relatively demanding equipment requirements, and have not been developed to industrial production

Method used

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  • Method for synthesizing 5,7-dihydroxy flavone

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Step 1: In a 1000ml three-necked reaction flask, add 168g of 1,3,5-trimethoxybenzene, 132g of aluminum trichloride, and 900ml of dichloroethane in sequence, and stir to dissolve. The temperature was controlled in an ice bath at 5°C, and 86 g of acetyl chloride was added dropwise, and the addition was completed within 20 minutes. After the addition, the temperature was raised to room temperature 25°C. Reacted for about 3.5 hours, poured the reaction solution into 2000ml of 5% hydrochloric acid ice solution, stirred for 30 minutes, statically separated and took the organic phase, washed with water until neutral, concentrated under reduced pressure to obtain the residue, and cooled to obtain intermediate 1, 199.5 g. Yield 95%.

[0034] Step 2: Add 13.5g of sodium methoxide powder and 67.5ml of methanol to a 500ml reaction bottle, and heat to reflux for 0.5h. Recover and distill methanol to obtain solid sodium methoxide. Then drop into intermediate 1,42g, methyl benzoat...

Embodiment 2

[0037] Step 1: In a 1000ml three-necked reaction flask, add 168g of 1,3,5-trimethoxybenzene, 158g of aluminum trichloride, and 800ml of dichloroethane in sequence, and stir to dissolve. The temperature was controlled in an ice bath at 5°C, and 93.6 g of acetyl chloride was added dropwise, and the addition was completed within 20 minutes. After the addition, the temperature was raised to room temperature 25°C. After reacting for about 3 hours, pour the reaction solution into 2000ml of 5% hydrochloric acid ice solution, stir for 30 minutes, and separate the layers to get the organic phase, wash with water until neutral, concentrate under reduced pressure to obtain the residue, and cool to obtain Intermediate 1, 182.7g . Yield 87%

[0038]The second step: in the 500ml reaction bottle, add sodium methoxide powder 18.9g, intermediate 142g, methyl benzoate 33g, toluene 350ml, stir, and connect the fractionation column on the reaction device. Heating started, and the temperature o...

Embodiment 3

[0041] Step 1: In a 1000ml three-necked reaction flask, add 168g of 1,3,5-trimethoxybenzene, 146g of aluminum trichloride, and 900ml of dichloromethane in sequence, and stir to dissolve. The temperature was controlled in an ice bath at 5°C, and 82 g of acetyl chloride was added dropwise, and the addition was completed within 20 minutes. After the addition, the temperature was raised to room temperature 25°C. After reacting for about 5 hours, pour the reaction solution into 2000ml of 5% hydrochloric acid ice solution, stir for 30 minutes, and separate the layers to get the organic phase, wash with water until neutral, concentrate under reduced pressure to obtain the residue, and cool to obtain Intermediate 1, 178.5g . Yield 87%.

[0042] Step 2: Add 21.6g of sodium methoxide powder and 108ml of methanol to a 500ml reaction bottle, and heat to reflux for 0.5h. Recover and distill methanol to obtain solid sodium methoxide. Then drop into intermediate 1,42g, methyl benzoate 33...

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Abstract

The invention discloses a method for synthesizing 5,7-dihydroxy flavone. The method comprises the following steps of: acetylating 1,3,5-trimethoxybenzene to generate 2,4,6-trimethoxybenzene ethyl ketone; condensing the 2,4,6-trimethoxybenzene ethyl ketone and methyl benzoate to generate 1-(2'-4'-6')-trimethoxy-3-phenyl-1,3-propanedione; and performing cyclization and demethylation on the 1-(2'-4'-6')-trimethoxy-3-phenyl-1,3-propanedione to prepare the 5,7-dihydroxy flavone so as to obtain chrysin. In the method, the 1,3,5-trimethoxybenzene is directly taken as a starting raw material, a target product is obtained by performing friedel-crafts acylation reaction, ester exchange, cyclization and demethylation, and the cyclization and the demethylation are performed in one step instead of two steps. The method has the advantages of low cost, low environmental pollution, low equipment requirement and mass production.

Description

technical field [0001] The invention belongs to the field of fine chemical drug synthesis, and in particular relates to a synthesis method of 5,7-dihydroxyflavone. Background technique [0002] 5,7-dihydroxyflavone, Chinese name chrysin, also known as chrysin. It mainly exists in the seeds and bark of the bignoniaceae plant wood butterfly and in the heart wood of the pinaceae plant mountain white pine and mangospine. However, because the content in the raw material is very low, the production value is not high, and there are few reports on the extraction and separation. At present, the research mainly focuses on the synthesis of chrysin. [0003] Cai Xiaohua, Hu Wei, etc. used phloroglucinol as the starting material to obtain the intermediate 2,4,6-trihydroxyacetophenone through Hoesch reaction with acetonitrile, and then condensed with benzoyl chloride to obtain β-propanedione, and then Rearrangement, ring closure to get chrysin. Xu Yangyan from Nanhua University used ph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30
Inventor 肖金霞郭文华肖红王晓莹
Owner SHAANXI JIAHE PHYTOCHEM
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