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Preparation process of alpha-damascenone

A preparation process, damascenone technology, applied in the field of α-damascenone preparation process, can solve the problems of expensive reagent yield, difficult to achieve mass production, strict conditions, etc., to avoid high operating costs, experimental Conditions and subsequent processing are easy and the effect of low preparation cost

Active Publication Date: 2018-09-21
UNIV OF SCI & TECH LIAONING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the early stage, Ohloff et al. used the Wharton rearrangement reaction to successfully synthesize α-Damascenone. Although the route is short, the product yield is low, and a large number of cyclization by-products will be generated at the same time, and subsequent processing is troublesome.
Stefano Serraand Claudio Fuganti et al. used α-ionone to synthesize a diol intermediate, and then used enzyme catalysis to synthesize α-Damascenone with a single configuration. At present, many patents have been authorized, but the conditions of the reaction Strict requirements, many steps, limited to laboratory operations
There are also researchers using (Me 3 Si) 2 The reagent CuLi.LiCN successfully synthesized α-Damascenone, but there are also problems such as many steps, expensive reagents and low yield, making it difficult to achieve mass production

Method used

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preparation example Construction

[0044]The preparation process of a kind of α-damascenone described in the present invention uses α-ionone, namely compound A, as a raw material, and reacts with hydroxylamine hydrochloride to obtain α-ionone oxime, namely compound B, and the double bond in compound B is oxidized After dehydration, α-ionone epoxidized oxime is compound C, and compound C is dehydrated under the action of acid to obtain α-ionone isoxazole derivative, which is compound D, and compound D is reduced to obtain the final product E, which is α-da Matone;

[0045] The structural formula of compound A:

[0046]

[0047] The structural formula of compound B:

[0048]

[0049] The structural formula of compound C:

[0050]

[0051] The structural formula of compound D:

[0052]

[0053] The structural formula of the final product E:

[0054]

[0055] Its reaction formula is as follows:

[0056]

[0057] The preparation technology of described a kind of α-damascenone, specifically com...

Embodiment 1

[0075] [Example 1] Synthesis of α-ionone oxime, compound B;

[0076] Take 10g, 0.052mol of α-ionone, that is, compound A, dissolve it with 20ml of ethanol, add it to the flask, add 3.8g, 0.06mol of hydroxylamine hydrochloride, 6.4g, 0.07mol of sodium acetate and 15ml of ionized water. After all the addition, the temperature of the system was raised to 55° C., and the reaction time was controlled for 3 hours. After the reaction, add 60ml of deionized water to the system, extract with ethyl acetate, combine the organic phases, and wash the organic phases with 10% saturated sodium bisulfite solution, anhydrous MgSO 4 After drying and rotary evaporation, an orange-yellow liquid was obtained, which was solid in a refrigerator, that is, α-ionone oxime, that is, compound B, and the yield was 99.6%.

[0077] The H NMR spectrum of α-ionone oxime, namely compound B, is as follows figure 1 Shown; α-ionone oxime is the carbon NMR spectrogram of compound B as figure 2 shown.

Embodiment 2

[0078] [Example 2] Synthesis of α-ionone epoxidized oxime, compound C;

[0079] After mixing 5 g and 0.024 mol of α-ionone oxime, that is, compound B, with 70 ml of methanol, they were added to the flask. Under stirring conditions, slowly add 35ml of 30% hydrogen peroxide and 5ml, 6mol / L lithium hydroxide mixture, after the addition, weigh 70mg of potassium carbonate, slowly add into the reaction system, maintain the system temperature at 25°C, and the reaction time is 15h . After the reaction is complete, add 150ml deionized water, extract with dichloromethane, combine the organic phases, and use anhydrous MgSO 4 After drying and rotary evaporation, the α-ionone epoxidized oxime, compound C, was obtained with a yield of 99.1%.

[0080] The H NMR spectrum of α-ionone epoxidized oxime, compound C, is as follows: image 3 Shown; α-ionone epoxidized oxime is the NMR carbon spectrogram of compound C as Figure 4 shown.

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Abstract

The invention relates to a preparation process of alpha-damascenone. The preparation process of the alpha-damascenone comprises the following steps: taking alpha-ionone, namely a compound A, as a rawmaterial, reacting the alpha-ionone with hydroxylamine hydrochloride to obtain alpha-oximes of ionones, namely a compound B; carrying out epoxidation on double bonds in the compound B to obtain alpha-epoxidized oximes of ionones, namely a compound C; dehydrating the compound C under the effect of acid to obtain alpha-ionone isoxazole derivative, namely a compound D; and carrying out reduction on the compound D to obtain a final product E which is the alpha-damascenone. The alpha-ionone is used as the raw material, the alpha-damascenone can be prepared by only four steps, the preparation process of the alpha-damascenone has the characteristics of short reaction period, low preparation cost, high yield of various steps and easiness in follow-up treatment, and is suitable for industrial production, and a gap of domestic industrial production of the product at present is filled.

Description

technical field [0001] The invention relates to a preparation process of α-damascenone, in particular to a process for synthesizing α-damascenone by using α-ionone as a raw material and being applicable to industrial preparation. Background technique [0002] Damascenone spices are compounds containing 13 carbon atoms and have a pleasant smell. They are a kind of precious spices that have developed rapidly in recent years and have been highly valued by scholars at home and abroad. Damascenone flavors generally include three isomers: α-damascenone, β-damascenone and γ-damascenone. Among them, the aroma of α-Damascenone is pleasant and pleasant, and it has a fruity aroma. It is not only used as a flavoring agent for some high-end cosmetics, but also often used in food flavors. With the maturation of flavoring technology, the application of α-Damascenone in tobacco has gradually increased. Among them, well-known high-end cigarettes such as Marlboro, Hainan, Jinlu and other bra...

Claims

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Application Information

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IPC IPC(8): C07C45/00C07C49/557C07D261/08C07D303/36C07D301/12C07C249/08C07C251/40
CPCC07C45/00C07C249/08C07D261/08C07D301/12C07D303/36C07C2601/16C07C49/557C07C251/40
Inventor 徐英黔胡君一肖国勇刘婧扬未兴福王龙龙郭爱强赵宏斌邱丽杰迟海军董岩张志强
Owner UNIV OF SCI & TECH LIAONING
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