ε-n-pentyl propionate-ε-caprolactone and its preparation method

A technology of n-pentyl propionate and n-pentyl acrylate, applied to the field of lactone-type fragrance compounds, ε-n-pentyl propionate-ε-caprolactone and its preparation, can solve the problem of low yield and low cost High, difficult ε-lactone type fragrance compounds and other issues

Active Publication Date: 2017-05-31
CHINA GATEWAY PHARMA DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Aiming at the technical problems in the prior art, the present invention provides a kind of ε-n-pentyl propionate-ε-caprolactone and its preparation method, the described ε-n-pentyl propionate-ε- Caprolactone and its preparation method solve the technical problems of difficulty in preparing ε-lactone type fragrance compounds, high cost and low yield in the prior art

Method used

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  • ε-n-pentyl propionate-ε-caprolactone and its preparation method
  • ε-n-pentyl propionate-ε-caprolactone and its preparation method
  • ε-n-pentyl propionate-ε-caprolactone and its preparation method

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Embodiment 1

[0032] A kind of synthetic method of n-pentyl acrylate compound, concrete steps are as follows:

[0033] In a 100ml round bottom flask, add 17.32g (0.19mol) of anhydrous toluene, 4.9g (0.01mol) of p-toluenesulfonic acid, 7.245g (0.10mol) of acrylic acid, 11.02g (0.13mol) of n-pentanol in Magnetic stirring and reflux at 110°C for 8 hours of reaction; after the reaction was completed, the reaction solution was cooled to room temperature, saturated aqueous sodium bicarbonate solution was added to the reaction solution, the organic phase was extracted with ethyl acetate, and the organic phase was washed three times with saturated brine. Anhydrous magnesium sulfate was dried, and the solvent was removed by rotary evaporation with a rotary evaporator. The product was obtained by thin-layer chromatography, and the eluent was PE:EA=8:1. The pure product was collected to finally obtain 12.87ml of transparent and colorless liquid. The rate is 94.2%.

[0034] The transparent colorless l...

Embodiment 2

[0038] The synthetic method of above-mentioned a kind of ε-propionate n-pentyl-ε-caprolactone compound, concrete steps are as follows:

[0039] Add 1.42g (0.01mol) of disodium hydrogen phosphate solid into a 50ml three-necked flask, replace with nitrogen three times, inject 13.25g (0.16mol) of dichloromethane, and inject 1.85g (0.013mol) of n-pentyl acrylate, 0.97 g (0.0064mol) 1-pyrrolidine-1-cyclohexene, after stirring for 30 minutes, slowly inject 0.86g (0.005mol) m-chloroperoxybenzoic acid solution dissolved in 13.25g (0.16mol) methylene chloride, in Complete within 10 minutes, under magnetic stirring, react for 4 hours; after the reaction is completed, put the three-neck flask into ice water to cool, add 15ml of normal temperature saturated sodium bicarbonate aqueous solution to the reaction solution to wash once, and wash twice with 30ml saturated sodium thiosulfate aqueous solution , washed twice with 95ml of 5% sodium hydroxide aqueous solution, twice with 50ml of dist...

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Abstract

The invention discloses an elpsilon-lactone perfume compound with a structure as described in the specification. The invention also discloses a preparation method for the elpsilon-lactone perfume compound. The preparation method comprises the following steps: with an acid compound and an alcohol compound as raw materials, subjecting the raw materials to esterification in an organic solvent under the action of an acid catalyst so as to obtain an amyl propionate compound; and with the amyl propionate compound and an alkene compound as raw materials carrying out addition and Baeyer-Villiger oxidation reaction under the action of an alkali catalyst and an acid catalyst so as to eventually obtain an elpsilon-amyl propionate-elpsilon-caprolactone compound. The novel elpsilon-lactone perfume compound with characteristic bouquet and fragrance of mellow and sweet rice wine is a novel research achievement of domestic and overseas research on elpsilon-lactone perfume compounds with characteristic fragrance.

Description

technical field [0001] The invention belongs to the field of chemical industry, and in particular relates to a lactone-type fragrance compound, in particular to ε-n-pentyl propionyl-ε-caprolactone and a preparation method thereof. Background technique [0002] Lactone-type fragrance compounds are ubiquitous in nature, and most of the lactone-type fragrance compounds can be obtained in nature. They are widely used in the formulation of food flavors and daily chemical flavors. They can be used as the main fragrance of flavors or as ingredients . Most of the lactone-type fragrance compounds have a low threshold value, so they are used sparingly in flavor formulations and have a strong aroma. The research on lactone-type fragrance compounds at home and abroad is generally on: γ-lactone-type fragrance compounds, δ-lactone-type fragrance compounds, and macrolide-type fragrance compounds. Among them, the γ-lactone type fragrance presents an obvious fruity aroma, the δ-lactone typ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D313/04
CPCC07D313/04
Inventor 易封萍黄俐
Owner CHINA GATEWAY PHARMA DEV CO LTD
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