Synthesis method of Megastigmatrienone

The technology of a kind of gigantotrienone and a synthetic method is applied in the synthesis field of gigantotrienone, can solve the problems such as no industrialized raw materials, low yield, difficult realization of industrialized production, etc., achieves thorough separation, high yield, and is beneficial to The effect of mass production

Inactive Publication Date: 2019-12-20
广州百花香料股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 2. Rowland uses dehydroionone as the raw material, sodium borohydride as the reducing agent, reduces the raw material to dehydroionol, and then rearranges it in acetone with dilute sulfuric acid to obtain 3-hydroxy-4,6,8-gianthan Enone, and finally oxidized with active manganese dioxide or chromium trioxide to obtain a cis-trans isomerization mixture of macrostigmatrienone; but the product dehydroionone has no industrial raw materials
[0007] 3. Li Shumian reduced crotonaldehyde with aluminum isopropoxide, brominated it with PBr3 in anhydrous pyridine at 0-15°C, and used anhydrous ether as a solvent under the protection of nitrogen, and reacted with lithium metal at reflux temperature. Lithium reagent, use TsOH as catalyst, benzene as dehydrating agent, let oxidized isophorone condense with ethylene glycol, due to steric effect,

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A synthetic method of macrostigmatrienone, comprising the steps of:

[0033] (1) Add 50.1g of special-grade alpha ionone and 1.5g of vanadyl acetylacetonate to 208.2g of acetone, stir and keep at 30-35°C, add tert-butyl hydroperoxide dropwise for 4 hours, and add 1.6g after the reaction Sodium thiosulfate quenched the reaction, vacuum recovered acetone, washed with brine 2 to 3 times, and anhydrous sodium sulfate suction filtered to remove water;

[0034] (2) Dissolve the dehydrated oil in step (1) in 50ml of absolute ethanol, add anhydrous calcium chloride, stir at 25°C for 30 minutes, add 5.2g of potassium borohydride in two batches, and react at constant temperature for 8-10 hours;

[0035] (3) Add 1.8g of p-toluenesulfonic acid directly to the reaction product of step (2), raise the temperature to 80-82°C and reflux for 4 hours. After the reaction, place it at room temperature and centrifuge to remove solids, then recover absolute ethanol to obtain 38.2g of giant be...

Embodiment 2

[0038] A synthetic method of macrostigmatrienone, comprising the steps of:

[0039] (1) Add 200.6g of super-grade alpha ionone and 6.0g of vanadyl acetylacetonate to 832.6g of acetone, stir and keep at 30-35°C, add tert-butyl hydroperoxide dropwise and react at constant temperature for 4 hours, and add 9.5g at the end of the reaction Sodium thiosulfate quenched the reaction, vacuum recovered acetone, washed with brine 2 to 3 times, and anhydrous sodium sulfate suction filtered to remove water;

[0040] (2) Dissolve the dehydrated oil in step (1) in 200ml of absolute ethanol, add anhydrous calcium chloride, stir at 25°C for 30 minutes, add 20.8g of potassium borohydride in two batches, and react at constant temperature for 8-10 hours;

[0041] (3) Add 7.1g of p-toluenesulfonic acid directly to the reaction product of step (2), raise the temperature to 80-82°C and reflux for 4 hours. After the reaction, place it at room temperature and centrifuge to remove solids, then recover a...

Embodiment 3

[0044] A synthetic method of macrostigmatrienone, comprising the steps of:

[0045] (1) Add 200.6g of super-grade alpha ionone and 6.0g of vanadyl acetylacetonate to 832.6g of acetone, stir and keep at 30-35°C, add tert-butyl hydroperoxide dropwise and react at constant temperature for 4 hours, and add 9.5g at the end of the reaction Sodium thiosulfate quenched the reaction, vacuum recovered acetone, washed with brine 2 to 3 times, and anhydrous sodium sulfate suction filtered to remove water;

[0046] (2) Dissolve the dehydrated oil in step (1) in 200ml of absolute ethanol, add anhydrous calcium chloride, stir at 25°C for 30 minutes, add 20.8g of potassium borohydride in two batches, and react at constant temperature for 8-10 hours. Suction filtration after the reaction, vacuum recovery of absolute ethanol to obtain borohydrogenated crude oil.

[0047] (3) Dissolve the borohydrogenated crude oil obtained in step (2) with 200ml of absolute ethanol, add 7.1g of p-toluenesulfon...

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PUM

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Abstract

The invention discloses a synthesis method of Megastigmatrienone. The method is characterized by comprising the steps: performing oxidation on alpha-ionone by using tert-butyl hydroperoxide under thecatalysis action of Vanadiumoxy Acetylacetonate so as to generate 3-oxo-alpha-ionone, performing hydroboration on 3-oxo-alpha-ionone in an ethanol solution so as to obtain 3-oxo-alpha-ionol, adding solid p-toluenesulfonic acid directly, and performing reflux dehydration so as to obtain Megastigmatrienone. The method has a simple process and simple conditions, and is more beneficial to industrialized production.

Description

technical field [0001] The invention belongs to the technical field of spices and fine chemicals, and in particular relates to a method for synthesizing macrostigmatrienone. Background technique [0002] Megastigmatrienone (chemical name: 3,5,5-trimethyl-4(2-butenylene)-2-cyclohexen-1-one, English name: Megastigmatrienone, CAS number: 13215-88- 8), there are four isomers, and what is usually obtained is a mixture of isomers. The content of the four isomers is 70%, which is an important neutral aroma component in tobacco. [0003] Macrostigmatrienone is a carotenoid degradation product, which is an important aroma-making substance in tobacco. It has tobacco aroma and spicy aroma, can significantly enhance the aroma of cigarettes, and improve the taste of smoking. It is widely used in perfumes, cosmetics, beverages and edibles. In essence. [0004] There are several methods for the synthesis of macrostigmatrienone at home and abroad: [0005] 1. Yu Juan dissolved α-ionol ac...

Claims

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Application Information

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IPC IPC(8): C07C45/66C07C45/79C07C49/647
CPCC07C45/66C07C45/79C07C29/143C07C45/28C07C2601/16C07C49/647C07C33/14
Inventor 胡林刚段艳张建斌庄子翀白济嘉吴习荧
Owner 广州百花香料股份有限公司
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