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Piperonal preparation method

A technology of jasmonal and catalyst, which is applied in the field of jasmonal preparation, can solve the problems of cumbersome treatment, high toxicity of chlorine gas, and many waste materials, and achieve the effects of simple process, low production cost and few by-products

Inactive Publication Date: 2017-12-05
ZHEJIANG NHU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In the first step of the method, the Friedel-Crafts reaction uses aluminum chloride or zinc chloride as a catalyst, and the post-reaction treatment is cumbersome and produces more waste; and the method uses highly toxic chlorine gas

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0032] In a 1L three-neck flask, add 500mL of dichloromethane, aluminum chloride / polystyrene (66.5g, loading capacity 10wt%), and slowly add acetyl chloride (42.9g, 5.5mol) dropwise under stirring conditions, and the dropwise addition is completed , then slowly drop piperonyl ring (61.0g, 0.5mol, dissolved in 100mL dichloromethane); Polystyrene catalyst; the reaction solution was extracted in layers, the organic layers were combined, the solvent was evaporated under reduced pressure, and the product was dried to obtain 77.2g, with a yield of 94%.

Embodiment 2

[0034] In a 1L three-necked flask, add 500mL of trifluoromethylbenzene, zinc chloride / aluminum trioxide (272.6g, loading capacity 10wt%), and slowly add acetic anhydride (56.1g, 0.55mol) dropwise under stirring conditions, drop After the addition is complete, slowly add piperonyl ring (61.0g, 0.5mol, dissolved in 100mL trifluoromethylbenzene); Zinc chloride / alumina catalyst; the reaction solution was extracted in layers, the organic layers were combined, the solvent was evaporated under reduced pressure, and the product was dried to obtain 73.9 g, with a yield of 90%.

Embodiment 3

[0036] In a 1L three-necked flask, add nitrobenzene 500mL, aluminum chloride / silicon dioxide (166.3g, loading capacity 10wt%), and slowly add acetic acid (33.0g, 0.55mol) dropwise under stirring condition, the dropwise addition is completed, Slowly add piperonyl ring (61.0g, 0.5mol, dissolved in 100mL nitrobenzene); Silicon oxide catalyst; the reaction solution was extracted in layers, the organic layers were combined, the solvent was evaporated under reduced pressure, and the product was dried to obtain 78.8g, with a yield of 96%.

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PUM

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Abstract

The invention discloses a piperonal preparation method. In the prior art, the method for preparing piperonal by using 1,3-benzodioxole as a raw material is used, wherein a large amount of hydrochloric acid is used so as to corrode the equipment and produce the environmental pollution problem, the reaction post-treatment is complicated, and more waste can be produced. The piperonal preparation method of the present invention comprises: 1) preparing 3,4-methylenedioxyacetophenone by using 1,3-benzodioxole and an acylation reagent as raw materials and using a supported aluminum chloride or zinc chloride catalyst through a Friedel-Crafts reaction; and 2) oxidizing the 3,4-methylenedioxyacetophenone by using a cuprous salt as a catalyst through a catalytic oxidation reaction to obtain the piperonal. According to the present invention, the piperonal preparation method has the total piperonal yield of up to about 93%, and has advantages of short reaction step, less by-product, high yield, easily available raw material, simple process, environment protection and low piperonal preparation cost, wherein the catalyst of the Friedel-Crafts reaction can be recycled.

Description

technical field [0001] The invention relates to the intermediates of flavors and fragrances and medicines and pesticides, in particular to a preparation method of jasmonal. Background technique [0002] Jasmonal is also called piperonal, and its chemical name is 3,4-dioxamethylenebenzaldehyde. [0003] Jasmonal is a precious spice, which not only has a sweet cherry and sunflower aroma, but also has a sweet heliotrope aroma, and also has a faint spicy aroma. Jasmonal is one of the main synthetic fragrances, which is widely used in the deployment of various flavors, and can also be used to develop dozens of other fragrances, pharmaceuticals and pesticides and other fine chemicals, such as piperonyl acetone, Xinyangjasmonal, Sesamol, jasmine nitrile, facidotril, pepper acetic acid, etc. [0004] Jasmonal has a wide range of uses, and the market demand is increasing year by year and its sales are not declining. The main raw material for the production of jasmonal is safrole e...

Claims

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Application Information

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IPC IPC(8): C07D317/54
CPCC07D317/54
Inventor 周有桂胡柏剡于明张玉红李其川
Owner ZHEJIANG NHU CO LTD
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