Synthesis method of (S)-(-)-alpha-damascenone

A synthetic method and technology of damascenone, which is applied in the field of synthesis of α-damascenone, can solve the problems of few specific synthesis studies and reports, difficult industrial production, complex and difficult synthetic methods, etc. The effect of high conversion rate and cheap and easy-to-obtain raw materials

Inactive Publication Date: 2015-05-20
ANHUI HYEA AROMAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] At present, there have been some reports abroad about the selective synthesis of a specific enantiomer of damascenone, but it is difficult to apply it to industrial production due to the complexity and difficulty of the synthesis method. There are few studies and reports on the specific synthesis of enantiomers, but through the olfactory test of damascenone spices with different optical isomerisms, it is found that the fragrance properties of different damascenone enantiomers have obvious differences, and they have significant Different characteristic aromas and olfactory thresholds

Method used

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  • Synthesis method of (S)-(-)-alpha-damascenone
  • Synthesis method of (S)-(-)-alpha-damascenone
  • Synthesis method of (S)-(-)-alpha-damascenone

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Embodiment 1

[0034] (1) Synthetic diols:

[0035] a. Add 50g of racemic α-ionone to 300ml of methanol, and continuously and slowly add 110ml of aqueous hydrogen peroxide solution with a mass concentration of 30% and 25ml of 6M hydrogen peroxide dropwise while the solution is cooled to 0°C and stirred. sodium solution. The mixed solution was stirred at 4°C for 6 days, and 50 ml of 30% hydrogen peroxide solution and 30 ml of methanol were additionally added dropwise every day. After the reaction, 300ml of water was added and extracted with ether. The organic phase was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The product α,β-epoxy-α-ionone was separated by column chromatography and recrystallized from hexane with a yield of about 81%.

[0036] b. Add 90ml of tetrahydrofuran, 30ml of water and 30ml of ethanol to the product obtained in the above step a, stir evenly at 0°C, then add a mixture of aluminum and mercury with a catalytic amount of 20mol% fo...

Embodiment 2

[0043] (1) Synthetic diols:

[0044] a. Add 70g of racemic α-ionone to 500ml of methanol, and continuously and slowly add 180ml of 30% hydrogen peroxide aqueous solution and 45ml of 6M sodium hydroxide aqueous solution dropwise while the solution is cooled to 0°C and stirred. The mixed solution was stirred at 4°C for 6 days, and 70 ml of 30% hydrogen peroxide solution and 50 ml of methanol were additionally added dropwise every day. After the reaction, 500ml of water was added and extracted with ether. The organic phase was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The product α,β-epoxy-α-ionone was separated by column chromatography and recrystallized from hexane with a yield of about 85%.

[0045] b. Add 150ml of tetrahydrofuran, 50ml of water and 50ml of ethanol to the product obtained in step a above, stir evenly at 0°C, then add a mixture of aluminum and mercury with a catalytic amount of 20 mol% for catalysis, and react at 0°C for...

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Abstract

The invention discloses a synthesis method of (S)-(-)-alpha-damascenone, which comprises the following steps: adding alpha-ionone into an alcohol or ether solvent, adding a hydrogen peroxide water solution and a sodium hydroxide water solution, stirring to perform double bond oxidization reaction to generate alpha,beta-epoxy-alpha-ionone, adding tetrahydrofuran, water and ethanol to generate beta-epoxy-alpha-ionone under the catalytic action of an aluminum-mercury mixture, carrying out ring-opening hydrogenation to generate 4-hydroxy-4-(2,6,6-trimethylcyclohexyl-2-alkenyl)-2-butanone, adding acetonitrile and an acetic acid solution to react with Me4NHB(OAc) to obtain a raw material diol, reacting the diol with vinyl acetate and methyl tert-butyl ether under the catalytic action of lipase while stirring to obtain an optical isomer diol, adding DMP (dimethylpyrazole) and CH2Cl2 to react to obtain propyl 1-methyl-3-oxo-3-(2,6,6-trimethyl-cyclohexyl-2-alkenyl)-acetate, and carrying out elimination reaction under the catalytic action of inorganic alkali to generate the (S)-(-)-alpha-damascenone dominant antipode. The method has the advantages of cheap and accessible raw materials, mild reaction conditions and higher conversion rate, is simple to operate, and can obtain the antipode with higher optical purity.

Description

technical field [0001] The invention relates to a synthesis method of damascenone, in particular to a synthesis method of (S)-(-)-α-damascenone. Background technique [0002] Damascenone, commonly known as Turkone or Rose Ketone, has a unique rose aroma, and in daily chemical fragrances, rose aroma is the most important and most commonly used floral aroma. Rose oil was used as early as two thousand years ago It is used as a spice, and it is still one of the expensive and rare spice varieties. Although damascenone spices came out late, they are valued by people because of their unique fragrance. Many countries have been devoting themselves to the research of their synthesis methods and techniques. Therefore, damascenone with the attractive sweet fragrance of roses The discovery and preparation of equine spices has great value. Damascenone mainly has the following 3 isomers: [0003] [0004] They have different characteristic aromas, among which α-Damascenone and β-Dama...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/26C07C45/64C07C49/557
CPCC12P7/26C07B2200/07C07C29/143C07C45/58C07C45/61C07C67/00C07C2601/16C07D301/12C07C49/557C07C69/145C07C33/14C07C49/242
Inventor 王天义汪民富董金龙徐基龙汪洋
Owner ANHUI HYEA AROMAS
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