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A kind of synthetic method of 3-l-menthoxypropane-1,2-diol

A technique for the synthesis of menthoxypropane and its synthesis method, which is applied in the preparation of ethers from alkylene oxides, chemical instruments and methods, and the preparation of organic compounds. Mild reaction conditions and high yield

Active Publication Date: 2016-03-30
KUNSHAN YAXIANG SPICEL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the asymmetry of epichlorohydrin, by-products
Therefore, it also poses a problem for purification

Method used

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  • A kind of synthetic method of 3-l-menthoxypropane-1,2-diol
  • A kind of synthetic method of 3-l-menthoxypropane-1,2-diol

Examples

Experimental program
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Effect test

Embodiment 1

[0013] Example 1, under nitrogen protection, menthol (156g, 1mol, 1eq) was added to a three-necked reaction flask filled with 300ml of anhydrous tetrahydrofuran, and when the internal temperature was lowered to 0-10°C, 60% NaH (48g, 1.2mol, 1.2eq), after the addition is complete, slowly raise the temperature to room temperature, stir at room temperature for 30-50min and then lower the temperature to 0-10°C, add 1,3-dichloroglycerol acetate dropwise (162.45g, 0.95mol, 0.95eq) tetrahydrofuran solution, dropwise completed, the temperature rose to 60 o C. Stir for 1-2 hours, drop to 0-15°C, add a certain amount of water dropwise, and add a catalytic amount of tetrabutylammonium iodide (3.2g), and raise the temperature to 60-70°C and stir for 3h. After the reaction is completed , extracted three times with n-hexane, 500ml each time, combined the three extracted organic layers, washed each 100ml with water and brine, washed the organic layer once, separated, dried, and distilled n-h...

Embodiment 2

[0014] Example 2, under nitrogen protection, menthol (300g, 1.92mol, 1eq) was added to a three-necked reaction flask containing 500ml of anhydrous tetrahydrofuran, and when the internal temperature was lowered to 0-10°C, 60% NaH (153.8 g, 3.84mol, 2eq), after the addition is complete, slowly raise the temperature to room temperature, stir at room temperature for 30-50min and then lower the temperature to 0-10°C, drop in 1,3-dichloroglycerolacetic acid Ester (328g, 1.92mol, eq) tetrahydrofuran solution, after dropping, raise the temperature to 60°C, stir for 1-2 hours, then drop to 0-15°C, drop a certain amount of water, and add a catalytic amount of tetrabutyl Ammonium iodide (6g, 2%), raise the temperature to 60-70°C and stir for 3h. After the reaction is completed, extract three times with n-hexane, 500ml each time, combine the three extracted organic layers, wash once with 200ml each of water and brine The organic layer was separated and dried, and the n-hexane and tetrahyd...

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Abstract

The invention relates to a synthesis method of 3-L-menthoxypropane-1,2-diol. The synthesis method comprises the steps of reacting menthol with 1,3-dihalo-glycerol acetate under a strong alkaline condition at a low temperature to generate 1-halo-2-acetoxy-3-L-menthoxypropane, dropwise adding a small amount of water, heating to hydrolyze acetyl, adding a phase transfer catalyst, carrying out cyclization to obtain 1,2-epoxy-ethyl-3-L-menthoxypropane, and hydrolyzing obtained 1,2-epoxy-ethyl-3-L-menthoxypropane under an acidic condition, so as to obtain 3-L-menthoxypropane-1,2-diol. The synthesis method has the beneficial effects that a synthesis process is easy, reaction conditions are mild, the operation is easy and convenient, the yield is high, and no side product is generated.

Description

technical field [0001] The invention relates to the field of chemistry and chemical engineering, in particular to a method for synthesizing 3-L-menthoxypropane-1,2-diol. Background technique [0002] 3-L-menthoxypropane-1,2-diol is a new type of cooling agent, which has a refreshing cool taste and is widely used in medicine, daily chemicals, food and tobacco products. In the preparation of cooling agent 3-L-menthoxypropane-1,2-diol, two methods are mainly used, the first method is to react menthol with benzyl glycidyl ether to obtain intermediate 1-benzyloxy- 3-L-menthoxypropane-2-alcohol, then hydrogenolysis to obtain the product, this route has by-product 1-benzyl in the preparation of intermediate 1-benzyloxy-3-L-menthoxypropane-2-alcohol Oxygen-2-L-menthoxypropane-3-alcohol is not easy to purify. Method 2: Menthol and epichlorohydrin react under Lewis acid catalysis to obtain the intermediate menthoxychloropropanol, which is then cyclized and hydrolyzed to obtain the p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/196C07C41/02
CPCC07C41/26C07C2601/14C07D301/26C07C43/196
Inventor 周军学
Owner KUNSHAN YAXIANG SPICEL CO LTD
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