Megastigmatrienone synthesis method

A technique for the synthesis of macrostigmatrienone and its synthesis method, which is applied in the field of synthesis of macrostigmatrienone, can solve problems such as increased production costs, and achieve the effects of low environmental pollution, strong industrial operability, and mild reaction conditions

Active Publication Date: 2010-05-26
YUNNAN REASCEND TOBACCO TECH GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this oxidation route also has some disadvantages. The use of ketone or ester reagents, especially the use of deionized water, increases the production cost; and the application of compressed air and oxygen systems puts forward higher requirements for production equipment.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Dissolve 23.6g of α-ionol acetate in 70ml of acetonitrile, add 13g of 70% tert-butyl hydroperoxide, add 1.34g of periodic acid under stirring at -5°C, and react for 8 hours. Separate the organic phase, wash the organic phase with water, and distill off the organic solvent to obtain 21.2 g of 3-oxo-α-ionol acetate.

[0019] The obtained 3-oxo-α-ionol acetate was dissolved in 60 ml of acetone, 0.4 g of sulfuric acid was added, and the mixture was refluxed for 5 hours. Evaporate off acetone and redissolve with ethyl acetate. Wash the organic phase with water to neutrality, and then distill off the organic solvent to obtain the crude macrostigmatrienone. The crude macrostigmatrienone was subjected to vacuum distillation, and the fractions at 86°C-120°C / 7-9mbar were collected to obtain 13.2 g macrostigmatrienone. The purity of macrostigmatrienone detected by GC-MS is 72.3%.

Embodiment 2

[0021] Dissolve 23.6g of α-ionol acetate in 70ml of ethyl acetate, add 10g of 70% tert-butyl hydroperoxide, add 1.73g of periodic acid under stirring at -10°C, and react for 8 hours. The organic phase was separated, washed with water, and the solvent was distilled off to obtain 19.6 g of 3-oxo-α-ionol acetate.

[0022] The obtained 3-oxo-α-ionol acetate was dissolved in 60 ml of acetone, 0.4 g of sulfuric acid was added, and the mixture was refluxed for 15 hours. Evaporate off acetone and redissolve with ethyl acetate. Wash the organic phase with water to neutrality, and then distill off the organic solvent to obtain the crude macrostigmatrienone. The crude macrostigmatrienone was subjected to vacuum distillation, and the fraction at 86°C-120°C / 7-9mbar was collected to obtain 12.27 g macrostigmatrienone. The purity of macrostigmatrienone detected by GC-MS is 73%.

Embodiment 3

[0024] Dissolve 23.6g of α-ionol acetate in 70ml of petroleum ether, add 13g of 70% tert-butyl hydroperoxide, add 1.92g of periodic acid under stirring at 15°C, and react for 8 hours. The organic phase was separated, washed with water, and the solvent was distilled off to obtain 15 g of 3-oxo-α-ionol acetate.

[0025] The obtained 3-oxo-α-ionol acetate was dissolved in 45 ml of acetone, 0.3 g of sulfuric acid was added, and the mixture was refluxed for 30 hours. Evaporate off acetone and redissolve with ethyl acetate. Wash the organic phase with water to neutrality, and then distill off the organic solvent to obtain the crude macrostigmatrienone. The crude macrostigmatrienone was subjected to vacuum distillation, and the fraction at 86°C-120°C / 7-9mbar was collected to obtain 10.15 g macrostigmatrienone. The purity of macrostigmatrienone detected by GC-MS is 62%.

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Abstract

The related synthesis method for megastigmatrienone comprises: with a little catalyst, using peroxide to oxygenize the alpha-violet acetate into 3-oxo-alpha-violet acetate with high yield; taking acidolysis and purification to obtain the objective product. This invention has no pollution of heavy metal, needs mild reaction condition, and fit to industrialization.

Description

technical field [0001] The invention relates to a method for synthesizing macrostigmatrienone. Background technique [0002] Due to the important contribution of macrostigmatrienone to the smoking taste of cigarettes, foreign scientists began to conduct in-depth research on its synthesis as early as the 1960s, and there were many documents and patents. In summary, there are mainly the following synthetic methods: [0003] 1. Rowland started from dehydroionone, reduced it to dehydroionol with sodium borohydride, then rearranged it with dilute sulfuric acid in acetone to obtain 3-hydroxy-4,6,8-macrostigmatriene, and finally used active dihydroionone Oxidation of manganese oxide or chromium trioxide to obtain cis-trans isomers; [0004] 2. Aasen et al. proposed that the isomers of macrostigmatrienone can be obtained from reflux of 3-oxo-α-ionol or its acetate in benzene in the presence of potassium bisulfate or p-toluenesulfonic acid; [0005] 3. Demole et al. prepared the i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/61C07C49/647C07C403/02C11B9/00
Inventor 谢冰刘欣宇孔宁川王保兴杨伟祖陈永宽
Owner YUNNAN REASCEND TOBACCO TECH GRP
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