Method for synthesizing cooling agent L-menthyl 3-hydroxybutyrate

A technology for the synthesis of hydroxybutyric acid, which is applied in the preparation of ester groups and hydroxyl groups, organic chemistry, etc., can solve the problems of high cost, complicated operation, and low yield, and achieve simple operation, high yield, and mild conditions Effect

Inactive Publication Date: 2009-05-06
上海香料研究所
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Problems solved by technology

High cost, complex operation, low yield

Method used

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  • Method for synthesizing cooling agent L-menthyl 3-hydroxybutyrate

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Embodiment Construction

[0008] The present invention is further illustrated below by way of examples.

[0009] 1. Preparation of L-menthyl acetoacetate

[0010] In a 500 ml three-necked flask equipped with a distillation device, 65.0 g (0.50 mol) of ethyl acetoacetate, 93.6 g (0.60 mol) of L-menthol, 2.65 g (0.025 mol) of sodium carbonate and 150 ml of toluene were added. Heating and distillation, about 4-5 hours. After the reaction is complete, wash with water until neutral. Toluene was recovered, and the remaining liquid was distilled under reduced pressure to obtain 116.0 g (98.5%) of the product, with a yield of 95.3%.

[0011] 2. Preparation of L-menthyl 3-hydroxybutyrate

[0012] In a 500 ml three-necked flask equipped with a stirrer, a thermometer and a reflux condenser, add 102.0 g (0.43 mol) of L-menthyl acetoacetate, 50 ml of methanol, cool to 10°C, and dropwise add 7.0 g (0.13 mol) of potassium borohydride. mol) and 35 ml of water, the dropwise addition temperature is controlled at 10-...

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Abstract

The invention discloses a synthetic method for 3-hydroxybutyric acid L-mint ester. The synthetic method comprises two steps: a first step, namely, a synthetic method for acetoacetic acid L-mint ester, which is characterized in that acetoacetic ester or methyl acetoacetate and L-mint camphor are subjected to ester exchange reaction under the action of a basic catalyst to prepare the acetoacetic acid L-mint ester, wherein the reaction time is 4 to 5 hours, the catalyst used in the reaction is sodium carbonate or potassium carbonate or calcium carbonate, and solvent used in the reaction is methyl benzene or benzene or cyclohexane; and a second step, namely, the acetoacetic acid L-mint ester is reduced to obtain the 3-hydroxybutyric acid L-mint ester, wherein the reaction temperature is between 10 and 20 DEG C, the solvent used in the reaction is methanol or ethanol, and a reducer in the reaction is potassium borohydride or sodium borohydride. The synthetic method has the advantages of easily obtained raw materials, mild conditions, simple and convenient operation, and high yield.

Description

technical field [0001] The invention relates to a synthesis method of 3-hydroxybutyrate L-menthyl. Background technique [0002] 3-Hydroxybutyrate L-menthyl is a new type of cooling agent. Since it has only a pure cooling taste, adding it to other products will not affect its fragrance, but it can increase its cooling feeling. The preparation of L-menthyl 3-hydroxybutyrate has two routes according to foreign literature: Route 1, ethyl acetoacetate and L-menthol carry out alcohol exchange reaction under the effect of acid catalyst, and the intermediate acetoacetate is obtained L-menthyl ester is then reduced to obtain the product; route 2, L-menthol is added to dipolyvinyl ketone to obtain the intermediate L-menthyl acetoacetate, and then reduced to obtain the product. The cost is high, the operation is complicated, and the yield is low. Contents of the invention [0003] The present invention aims at the above problems and provides a synthetic method of 3-hydroxybutyrate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/675C07C67/03
Inventor 章平毅陆欢沈蔚
Owner 上海香料研究所
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