Preparation method of syn-p-menthyl-3,8-diol

A technology for menthyl and cis, which is applied in the field of preparation of chemical drugs, can solve the problems of low yield and achieve the effects of simple preparation process, high conversion rate and high product purity

Inactive Publication Date: 2017-02-08
ZHANG JIA GANG VINSCE BIO PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

High-quality p-menthyl-3,8-diol does not contain or contain a small amount of trans structure, which requires that the product configuration should be controlled as much as possible during synthesis, so as to make the separation and purification steps simple and maintain a high yield, application number In 2013100826252, a directional synthesis method of cis-menthyl-3,8-diol is proposed, the steps are simple, but the yield is still low

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] This example provides a kind of cis-p-menthyl-3, the preparation method of 8-diol, concrete implementation is as follows:

[0013] Add 50L of deionized water into a 150L stainless steel reaction kettle, weigh 8kg of citronellal, 120g of sodium p-toluenesulfonate, and 96g of benzyltriethylammonium chloride and put them into the reaction kettle, and then blow nitrogen into the reaction kettle Oxygen, stirred and reacted at room temperature, adjusted the pH of the reaction system to 3, and detected and analyzed it with TCL. Water with potassium carbonate to adjust the pH to neutral.

[0014] The reaction solution was allowed to stand for stratification, the organic phase was separated, and then washed with deionized water, the organic phase was collected, and dried overnight with 1 kg of anhydrous sodium sulfate. After drying, the organic phase obtained by filtering is placed in a 25L rectification device. The rectification tower is filled with no glass springs, the heigh...

Embodiment 2

[0016] This example provides a kind of cis-p-menthyl-3, the preparation method of 8-diol, concrete implementation is as follows:

[0017] Add 80L of deionized water into a 150L stainless steel reactor, weigh 10kg of citronellal, 150g of sodium p-toluenesulfonate, and 170g of benzyltriethylammonium chloride, and put them into the reactor, and then blow nitrogen into the reactor Oxygen, stirred and reacted at 40°C, adjusted the pH of the reaction system to 2.5, tested and analyzed with TCL, stopped the reaction after the reaction was complete, and quickly poured ice salt water into the jacket of the reaction kettle to cool the reaction system to 0°C, and then Anhydrous potassium carbonate was added to adjust the pH to neutral.

[0018] The reaction solution was allowed to stand for stratification, the organic phase was separated, and then washed with deionized water, the organic phase was collected, and dried overnight with 1 kg of anhydrous sodium sulfate. After drying, the or...

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PUM

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Abstract

The invention discloses a preparation method of syn-p-menthyl-3,8-diol. The preparation method comprises the following steps of adopting citronellal as a raw material, carrying out cyclization reaction in a water solution with the temperature of 20 to 50 DEG C and pH of 2 to 4 under the action of para-toluenesulfonic acid sodium salt and benzyl triethyl ammonium chloride, and obtaining the syn-p-menthyl-3,8-diol as a product after complete reaction, wherein the feeding quality of the para-toluenesulfonic acid sodium salt is 1 percent to 1.5 percent of the feeding quality of the citronellal, and the feeding quality of the benzyl triethyl ammonium chloride is 1 percent to 2 percent of the feeding quality of the citronellal. The preparation process is simple and environmental-friendly, the prepared product has good purity which can achieve not less than 99 percent, and the conversion rate is high.

Description

technical field [0001] The invention relates to the preparation of chemical drugs, in particular to a preparation method of cis-p-menthyl-3,8-diol. Background technique [0002] P-menthyl-3,8-diol (also known as: menthane-3,8-diol, p-menthane-3,8-diol, English abbreviation: PMD, p-menthane-3,8-diol), due to its low melting point, Widely used as a cooling agent in food additives. In medicine, it is mainly added to pharmaceutical excipients to promote the transdermal absorption of drugs. In terms of cosmetics, it also mainly promotes transdermal absorption, and also has anti-inflammatory and anti-itching effects. Daily chemicals and pesticides are mainly used for repellants and insecticides. The natural p-menthyl-3,8-diol is mainly derived from Eucalyptus citriodora, a eucalyptus tree in Australia. The key mosquito repellent ingredient containing natural p-menthyl-3,8-diol is also called lemonamine oil, and the product name is citriodiol. At present, the global demand for ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C35/08C07C29/00
CPCC07C29/00
Inventor 彭学东张梅赵金召闫勇义
Owner ZHANG JIA GANG VINSCE BIO PHARM
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