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Preparation method of 5-methyl-2-heptylene-4-one

A technology of methyl and heptene, which is applied in the field of preparation of 5-methyl-2-hepten-4-one, can solve the problems of cumbersome operation, long reaction time, and difficulty in industrial production, and avoid oxidation reaction, operate Simple, pollution-reducing effect

Inactive Publication Date: 2016-10-26
GUANGXI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In order to solve the technical problems in the above-mentioned preparation method of 5-methyl-2-hepten-4-one, such as heavy pollution, cumbersome operation, long reaction time, low yield, and difficulty in industrialized production, the present invention provides a A preparation method of spice 5-methyl-2-hepten-4-one with a nutty aroma using gamma-butyrolactone as a raw material. The method has the advantages of low pollution, simple operation and high yield, and is suitable for industrial production

Method used

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  • Preparation method of 5-methyl-2-heptylene-4-one

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Embodiment 1

[0037] Embodiment 1: Preparation of 2-sec-butyl-2-hydroxytetrahydrofuran:

[0038] In a 500mL three-necked flask equipped with stirring, condenser, thermometer and dropping funnel, add 0.3mol / 7.2g of Mg activated by hydrochloric acid, two grains of iodine, then add 60mL of tetrahydrofuran dehydrated, and then add 34.3g of 2-bromobutyl Mixed solution of alkane (0.25mol) and 150mL tetrahydrofuran 30mL mixed solution, add the remaining part after triggering, keep slight boiling, reflux for 2 hours after addition, after the reaction is complete, add 17.3g γ-butyrolactone (0.2mol) and 50mL Mixed solution of tetrahydrofuran, keep slightly boiling, reflux for 2 hours after addition, after reaction is complete, add saturated NH 4 Quenched by Cl, extracted with ethyl acetate three times, washed with saturated NaCl, washed with water, dried over anhydrous sodium sulfate, concentrated under reduced pressure, purified by column chromatography to obtain 21 g of 2-sec-butyl-2-hydroxytetrahy...

Embodiment 2

[0039] Embodiment 2: Preparation of 2-sec-butyl-2-hydroxytetrahydrofuran:

[0040] In a 1000mL three-necked flask equipped with stirring, condenser, thermometer and dropping funnel, add Mg0.6mol / 14.4g activated by hydrochloric acid, two grains of iodine, then add 100mL of dehydrated tetrahydrofuran, and then add 68.5g of 2-bromobutyl Mixed solution of alkane (0.5mol) and 300mL tetrahydrofuran 60mL mixed solution, add the remaining part after triggering, keep slightly boiling, reflux for 2 hours after addition, after the reaction is complete, add 34.5g γ-butyrolactone (0.4mol) and 100mL Mixed solution of tetrahydrofuran, keep slightly boiling, reflux for 2 hours after addition, after reaction is complete, add saturated NH 4 Quenched by Cl, extracted 3 times with ethyl acetate, washed with saturated NaCl, washed with water, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography to obtain 40.4 g of 2-sec-butyl-2-hydroxytetr...

Embodiment 3

[0041] Embodiment 3: Preparation of 2-sec-butyl-2-hydroxytetrahydrofuran:

[0042]In a 2000mL three-necked flask equipped with stirring, condenser, thermometer and dropping funnel, add Mg1.2mol / 28.8g activated by hydrochloric acid, two grains of iodine, then add 200mL of tetrahydrofuran dehydrated, and then add 137g of 2-bromobutane (1mol) and 500mL tetrahydrofuran mixed solution 80mL mixed solution, add the remaining part after triggering, keep a slight boil, reflux for 2 hours after the addition, after the reaction is complete, add dropwise a mixture of 69g γ-butyrolactone (0.8mol) and 150mL tetrahydrofuran Solution, keep slightly boiling, reflux for 2 hours after addition, after the reaction is complete, add saturated NH 4 Quenched by Cl, extracted with ethyl acetate three times, washed with saturated NaCl, washed with water, dried over anhydrous sodium sulfate, concentrated under reduced pressure, purified by column chromatography to obtain 81 g of 2-sec-butyl-2-hydroxytet...

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Abstract

The invention discloses a preparation method of 5-methyl-2-heptylene-4-one. The preparation method comprises the following steps of using gamma-butyrolactone as raw material, and reacting with sec-butylmagnesium bromide, so as to obtain a 2-sec-butyl-2-hydroxytetrahydrofuran intermediate; dewatering, so as to obtain a 5-sec-butyl-2,3-dihydrofuran intermediate; catalyzing, and opening loop, so as to obtain 1-hydroxyl-5-methyl-4-heptanone; dewatering, and shifting double bonds, so as to obtain a product of 5-methyl-2-heptylene-4-one. The preparation method has the advantages that the used gamma-butyrolactone and sec-butyl bromide are commodity products, so that the obtaining of reaction raw materials is easy, and the cost of raw materials is low; in addition, the chemical metering for oxidization reaction is avoided, the pollution is little, the operation is simple, the purity of the product is high, and the preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to a new synthesis process of perfume, in particular to a preparation method of 5-methyl-2-hepten-4-one. Background technique [0002] 5-Methyl-2-hepten-4-one, also known as Hazelnutone. It is a very valuable edible and daily spice, with good taste, nutty aroma at high concentration, and aroma enhancing effect at low concentration, it can be widely used in food, beverage, oral products and feed Among additives, it can also be used in aerosols, detergents and cosmetics. [0003] The preparation method of 5-methyl-2-hepten-4-one at present is as follows according to bibliographical reports: [0004] (1) The US patent (US4563365) uses sec-butylmagnesium bromide and crotonaldehyde to obtain the intermediate 5-methyl-2-hepten-4-ol through Grignard reaction, and then chemically oxidizes it with sodium dichromate to obtain the product. However, the first step of this method will produce by-products of 1,4 addition, and the second step...

Claims

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Application Information

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IPC IPC(8): C07C49/203C07C45/66C07C45/67
CPCC07C45/66C07C45/59C07C45/67C07D307/20C07D307/28
Inventor 王立升秦健峰罗轩刘旭蒋敏捷
Owner GUANGXI UNIV
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