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Preparation method of 7-methoxyflavone

The technology of methoxyflavonoid and benzoyl chloride is applied in the field of preparation of 7-methoxyflavonoid, can solve the problems of reduced product yield, complicated preparation process, loss and the like, and achieves easy industrial production, pollution-free yield, Easy-to-use effects

Inactive Publication Date: 2016-11-09
JIAXING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation process of this process is complex and requires multiple column passes, which will cause indispensable losses, reduce product yield, increase production costs, and cannot meet the needs of producers.

Method used

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  • Preparation method of 7-methoxyflavone
  • Preparation method of 7-methoxyflavone
  • Preparation method of 7-methoxyflavone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 16.6 grams (0.1mol) of paeonol, 15.2 grams (0.15mol) of triethylamine and 50 milliliters of tetrahydrofuran (THF) in a 250 mL three-neck round bottom flask, and dissolve 14.7 grams (0.105 mol) of benzoyl chloride in 20 milliliters of tetrahydrofuran at room temperature Slowly add dropwise, control the temperature at about 30 degrees, continue to react for 1 hour after the dropwise addition is completed, remove the triethylamine hydrochloride generated by simple filtration, re-add the filtrate in the original three-necked flask, and add 13.5g (0.12 mol) Potassium tert-butoxide, continue to react for 0.5 hour after adding, add dibutyl tin oxide (accounting for 10% of paeonol mass) after the reaction is completed, and react the reaction mixture for 3 hours in stirring reflux. After the reaction was completed, dibutyltin oxide was removed by filtration while it was hot, and the filtrate was concentrated to obtain the crude product of 7-methoxyflavone, which was recrystal...

Embodiment 2

[0027] Add 16.6 grams (0.1mol) of paeonol, 15.2 grams (0.15mol) of triethylamine and 50 milliliters of tetrahydrofuran in a 250 mL three-neck round bottom flask, and dissolve 25.3 grams of benzoyl chloride (0.18 mol) in 40 milliliters of tetrahydrofuran at room temperature Slowly add dropwise, control the temperature at about 20 degrees, continue to react for 1.5 hours after the dropwise addition, remove the triethylamine hydrochloride generated by simple filtration, re-add the filtrate in the original three-necked flask, add 14.6g (0.13 mol) Potassium tert-butoxide, continue to react for 0.7 hours after the addition, add dibutyl tin oxide (accounting for 20% of paeonol mass) after the reaction, and react the reaction mixture for 12 hours in stirring reflux. After the reaction was completed, dibutyltin oxide was removed by filtration while it was hot, and the filtrate was concentrated to obtain the crude product of 7-methoxyflavone, which was recrystallized from absolute ethano...

Embodiment 3

[0029] Add 16.6 grams (0.1mol) of paeonol, 15.2 grams (0.15mol) of triethylamine and 60 milliliters of tetrahydrofuran in a 250 mL three-neck round bottom flask, and dissolve 19.7 grams (0.14 mol) of benzoyl chloride in 30 milliliters of tetrahydrofuran at room temperature Slowly add dropwise, control the temperature at about 25 degrees, continue to react for 2 hours after the dropwise addition is completed, remove the triethylamine hydrochloride generated by simple filtration, re-add the filtrate to the original three-necked flask, and add 13.5g (0.12 mol) Potassium tert-butoxide, continue to react for 0.7 hours after the addition, add dibutyltin oxide (accounting for 5% of paeonol mass) after the reaction, and react the reaction mixture for 8 hours under stirring reflux. After the reaction was completed, dibutyltin oxide was removed by filtration while it was hot, and the filtrate was concentrated to obtain crude 7-methoxyflavone, which was recrystallized from absolute ethano...

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Abstract

The invention discloses a preparation method of 7-methoxyflavone and belongs to the field of chemical synthesis. The preparation method comprises that paeonol and benzoyl chloride as raw materials undergo an esterification reaction in the presence of triethylamine base, then the reaction mixed solution is subjected to simple suction filtration so that triethylamine hydrochloride is removed, potassium tert-butoxide is directly added into the filtrate, the mixture undergoes a reaction at the normal temperature, dibutyltin oxide is added into the reaction product, and the formed reaction mixed solution is subjected to heating backflow dehydration so that 7-methoxyflavone is obtained. The technical route has the characteristics of less process, operation simpleness, no pollution, desiccant reuse and industrial production easiness. The preparation method is an economic and simple 7-methoxyflavone preparation method.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and more specifically relates to a preparation method of 7-methoxyflavone. Background technique [0002] 7-methoxyflavone is a kind of flavonoids with strong biological activity, which has the functions of preventing and treating diabetes, anti-cancer, anti-inflammation, anti-oxidation, anti-mutagenesis and cardiovascular. Because natural 7-methoxyflavone compounds are limited by natural content, and there are certain difficulties in separation and purification. Therefore, the research on the chemical synthesis of 7-methoxyflavone has important practical significance. [0003] The reported methods for the synthesis of 7-methoxyflavone mainly use the Baker-Venkataraman method, Rries rearrangement, iodine catalysis, solid-phase supported catalysis, microwave-assisted synthesis, and organic base DBU catalyzed cyclization, etc., but these methods all exist The shortcomings of long route, low total...

Claims

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Application Information

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IPC IPC(8): C07D311/60
CPCC07D311/60
Inventor 宗乾收汪剑波宋熙熙张洋周宏伟包琳张新克
Owner JIAXING UNIV
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