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Production method of 1'-acetoxyl chavicol acetic ester

A technology of acetoxypiperol acetate and production method, which is applied in the field of 1'-acetoxypiperol acetate production, can solve the problems of poor reaction quality and low yield, and achieve complete reaction and high yield. High, easy-to-operate effect

Inactive Publication Date: 2012-12-26
HONGYI SCI & TECH CO LTD NANCHANG
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  • Abstract
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Problems solved by technology

[0007] JP2006206541A discloses the synthesis of compound 1'-(s)-acetoxypiperol acetate by the method of acetylation after the reaction of p-hydroxybenzaldehyde and vinylmagnesium bromide, but the reaction quality is poor and the yield is low

Method used

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  • Production method of 1'-acetoxyl chavicol acetic ester
  • Production method of 1'-acetoxyl chavicol acetic ester
  • Production method of 1'-acetoxyl chavicol acetic ester

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Experimental program
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Embodiment Construction

[0026] 1. Preparation of 4-(1-hydroxy-4-butene)-phenol

[0027] Take p-hydroxybenzaldehyde and propenyllithium and add them to a multifunctional reaction kettle with a special bottom valve, add ether, stir and react, and let stand.

[0028] Separate the organic phase and add anhydrous sodium sulfate to dry it, filter it with a special filter, and recover diethyl ether by distillation to obtain 4-(1-hydroxy-4-butene)-phenol with a yield of 96%.

[0029] 2. Preparation of crude product of 1'-acetoxypiperol acetate

[0030] Take 4-(1-hydroxy-4-butene)-phenol, acetic anhydride, anhydrous pyridine, and 4-dimethylaminopyridine, put them in a multifunctional reaction kettle with a special bottom valve, stir, and set the temperature at 90°C to 110°C React for 8 to 10 hours, stop heating, stir and react at room temperature for 8 to 10 hours, add water and stir for 1 hour, add toluene and stir for 1 hour, add hydrochloric acid solution and stir for 2 hours, let stand, separate the tolu...

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Abstract

The invention discloses a method for producing 1'-acetoxyl chavicol acetic ester, comprising the following steps of: by using a multifunctional reaction kettle provided with a purpose-made kettle bottom valve as a reactor and using a purpose-made filter as refining equipment, reacting hydroxyl benzaldehyde with propenyl lithium to generate 4-(1-hydroxyl-4-butene)-phenol, then performing acetylation reaction, and refining and drying to produce the 1'-acetoxyl chavicol acetic ester. Compared with the traditional method for producing the 1'-acetoxyl chavicol acetic ester by using synthesis equipment, the production method of the 1'-acetoxyl chavicol acetic ester has the advantages of few reaction steps, mild reaction condition, convenient refining, simple operation, and good heat preservation, oxidation prevention, tightness and environmental protection effect of the used purpose-made equipment and complete reaction, and the reaction equipment has the advantages of simple structure, convenient operation, easy disassembly, assembly and cleaning, high filtering efficiency, reaction quality and yield and stable product quality.

Description

technical field [0001] The present invention relates to the field of medicine and chemical industry, more specifically, relate to a kind of 1'-acetoxypiperol acetate production method. Background technique [0002] The English name of 1’-acetoxychavicol acetate (ACA) is 1’-acetoxychavicol acetate (ACA), and the molecular formula is C 13 h 14 o 4 , the molecular weight is 234.25, and the structural formula is [0003] Chinese patent ZL031308767 reports that 1'-acetoxypiperol acetate, isolated and purified from the dry rhizome of Alpinia galanga Willd. of Zingiberaceae plant, has the ability to inhibit HIV-1 NL43 in MT-4 cells. Replication, but no effect on the survival of MT-4 cells, showing high safety and the characteristics of inhibiting the extranuclear migration of HIV Rev protein, as a Rev protein inhibitor, it has significant anti-HIV-1 infection activity. [0004] There are also research reports showing that 1'-acetoxypiperol acetate has antitumor properties (Mo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/16C07C67/08
Inventor 刘孝乐许军钱进陶琳马临
Owner HONGYI SCI & TECH CO LTD NANCHANG
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