Preparation method of 3,7-dimethyl-3-acetylthio-6-octenol

A technology of acetylthio and dimethyl, applied in the field of preparation of 3,7-dimethyl-3-acetylthio-6-octenol, which can solve the problem of harsh reaction conditions, unfriendly environment and many by-products and other problems, to achieve the effect of short reaction time, low price and low production cost

Inactive Publication Date: 2018-11-16
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has harsh reaction conditions, is not fri...

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  • Preparation method of 3,7-dimethyl-3-acetylthio-6-octenol

Examples

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Embodiment 1

[0027] A preparation method of 3,7-dimethyl-3-acetylthio-6-octenol, comprising the following steps:

[0028] (1), at room temperature, 2.02 grams (98.90%, 8.76mmol) 3,7-dimethyl-3-acetylthio-6-octenal, 0.33 grams (8.76mmol) sodium borohydride and 20mL water The mixed solution A formed was stirred and reacted for 5 hours, and the resulting reaction solution was washed with a 10% HCl aqueous solution by mass percentage, and the pH of the washing was neutral;

[0029] (2), step (1) pH washing to neutral reaction solution is extracted with ether, and the organic layer of gained is washed with anhydrous MgSO 4 Dry and filter with filter paper the next day, and the resulting filtrate is evaporated and concentrated by a rotary evaporator to obtain 1.78 g of crude product 3,7-dimethyl-3-acetylthio-6-octenol, which is detected by gas chromatography. The purity is 96.80%, and the yield is 85.30%;

[0030] (3), the crude product of 3,7-dimethyl-3-acetylthio-6-octenol obtained in step (...

Embodiment 2

[0034] A preparation method of 3,7-dimethyl-3-acetylthio-6-octenol, comprising the following steps:

[0035] (1), at room temperature, mix 8.20 grams (98.90%, 35.56mmol) 3,7-dimethyl-3-acetylthio-6-octenal, 1.07 grams (28.30mmol) sodium borohydride and 20mL water The mixed solution A formed was stirred and reacted for 3 hours, and the resulting reaction solution was washed with an aqueous HCl solution with a mass percent concentration of 10%, until the pH of the washing was neutral;

[0036] (2), step (1) pH washing to neutral reaction solution is extracted with ether, and the organic layer of gained is washed with anhydrous MgSO 4 Dry and filter with filter paper the next day, and the resulting filtrate is evaporated and concentrated by a rotary evaporator to obtain 6.79 g of crude product 3,7-dimethyl-3-acetylthio-6-octenol, which is detected by gas chromatography. The purity is 97.00%, and the yield is 80.52%;

[0037] (3), the crude product of 3,7-dimethyl-3-acetylthio-6-o...

Embodiment 3

[0039] A preparation method of 3,7-dimethyl-3-acetylthio-6-octenol, comprising the following steps:

[0040] (1), at room temperature, mix 8.15 grams (98.90%, 35.35mmol) 3,7-dimethyl-3-acetylthio-6-octenal, 0.67 grams (17.72mmol) sodium borohydride and 30mL water The mixed solution A formed was stirred and reacted for 2.5 hours, and the resulting reaction solution was washed with a 10% HCl aqueous solution by mass percentage, and the pH of the washing was neutral;

[0041] (2), step (1) washes the reaction liquid of pH to neutrality and extracts with ether, and the organic layer of gained is washed with anhydrous MgSO 4 Dry and filter with filter paper the next day, and the obtained filtrate is evaporated and concentrated by a rotary evaporator to obtain 6.43g of crude product of 3,7-dimethyl-3-acetylthio-6-octenol, which is detected by gas chromatography. is 96.38%, and the yield is 76.23%;

[0042] (3), the crude product of 3,7-dimethyl-3-acetylthio-6-octenol obtained in s...

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Abstract

The invention relates to a preparation method of 3,7-dimethyl-3-acetylthio-6-octenol. The preparation method comprises the following steps: (1) stirring 3,7-dimethyl-3-acetylthio-6-octenal and sodiumborohydride in a mole ratio being 4:1-3:1 in an aqueous solvent at room temperature for reaction for 2-5 hours, and performing washing with an acid aqueous solution until pH is 7; (2) extracting a reaction solution washed to be neutral in the step (1) with an extracting agent, and drying and concentrating the extracted organic phase to obtain a crude product; (3) purifying the crude product obtained in step (2) to obtain a 3,7-dimethyl-3-acetylthio-6-octenol pure product. Compared with the prior art, the preparation method has the advantages of easily available raw materials, simple preparation process and low cost, and is convenient to operate, environmentally friendly and suitable for industrial production, and the problems of environmental unfriendliness, long reaction route and low yield which are caused by adoption of pyridine and thioacetic acid of traditional methods are solved.

Description

[technical field] [0001] The invention relates to the technical field of preparation of monoterpene sulfur-containing spices, in particular to a preparation method of 3,7-dimethyl-3-acetylthio-6-octenol. [Background technique] [0002] 3,7-Dimethyl-3-acetylthio-6-octenol, a colorless liquid, is a monoterpenoid alcohol compound. At the same time, it is also a monoterpene sulfur-containing fragrance compound, which is a very useful fragrance And pharmaceutical intermediates, but also an important component of tropical plants and fruits. There are few reports on the preparation of this compound. [0003] In 2015, American scientist Robert J.Canon et al. (Identification, Synthesis, and Characterization of Novel Sulfur-Containing Volatile Compounds from the In-Deph Analysis of Lisbon Lemon Peels[J], 2015,63:1915-1931) used citral as raw material , At 0°C, use pyridine as base, citral and thioacetic acid for 1,4 addition reaction to obtain 3,7-dimethyl-3-acetylthio-6-octenal. T...

Claims

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Application Information

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IPC IPC(8): C07C327/28
CPCC07C327/28
Inventor 杨始刚张钰琳
Owner SHANGHAI INST OF TECH
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