Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for synthesizing farnesol

A synthesis method and technology of farnesol, applied in the direction of reduction and preparation of oxygen-containing functional groups, can solve the problems of unstable reaction, long route, expensive reagents, etc., and achieve the effects of cost reduction, safe reaction route and high purity

Inactive Publication Date: 2012-05-02
SHANGHAI RECORD PHARM CO LTD +1
View PDF0 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The route of the method described in the literature is too long, the reaction is unstable, and quite a few reagents are expensive, so they cannot be used in industrial production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for synthesizing farnesol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0031] Below in conjunction with specific embodiment further illustrate how the present invention is realized:

[0032] step one:

[0033] In a 3000 ml four-neck flask, add 462 g of geraniol and 1900 ml of dichloromethane, add 223.2 g of dimethyl sulfide dropwise under stirring, keep the system <0°C, keep stirring for 15 min, and add 422 g of NCS in batches , kept at -5-5°C and stirred for 2 h, followed by TLC until the reaction was complete. The filtrate obtained by filtration was washed with 2000 ml of water, the water phase was added with 500 ml of dichloromethane for back extraction, the combined organic phase was washed once with 2000 ml of 5% sodium bicarbonate aqueous solution, and once again with 1500 ml of sodium chloride aqueous solution, and the organic phase was dried and concentrated 550 g of geranyl chloride was obtained, which was directly used in the next reaction. The purity is 85%, and the yield is 90%.

[0034] Step two:

[0035] In a 3000 ml four-ne...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
densityaaaaaaaaaa
boiling pointaaaaaaaaaa
flash pointaaaaaaaaaa
Login to View More

Abstract

The invention discloses a method for synthesizing farnesol. The method has the characteristics of low cost, safe reaction route, environment friendliness and high purity of an obtained product. The method comprises the following steps of: 1, reacting geraniol (E)-3,7-dimethyl-2,6-octadiene-1-alcohol with dimethyl sulfide and N-chloro succimide in dichloromethane to obtain geranyl chloride; 2, reacting the geranyl chloride with ethyl acetoacetate under the action of potassium carbonate to obtain geranyl ethyl acetoacetate, adding sodium hydroxide after the reaction is finished, heating for decarboxylation, and thus obtaining geranyl acetone; 3, introducing acetylene gas into the geranyl acetone under the action of inorganic base, and reacting to obtain (E)-3,7,11-trimethyl dodecane-6,10-diene-1-alkyne-3-alcohol; 4 and 5, obtaining (E)-3,7,11-trimethyl-1,2,6,10-tetraalkenyl acetate; 6, hydrolyzing the (E)-3,7,11-trimethyl-1,2,6,10-tetraalkenyl acetate to obtain farnesal; and 7, reducing the farnesal in methanol by using sodium borohydride to obtain the farnesol.

Description

technical field [0001] The invention relates to a method for synthesizing farnesol. The scientific name of farnesol is (E)-2,6,10-trimethyl-2,6,10-dodecatrien-12-ol. Background technique [0002] Farnesol shown in compound 1 is an important spice and food additive, and also an important starting material for many pharmaceutically active molecules. It is prepared from compound 2 geraniol through a seven-step reaction. [0003] [0004] It has been reported that the Wittig reaction is used as the key step to obtain compound 1, and there are reports in the literature that the coupling reaction of methyl copper reagent is used as the key step to obtain compound 1. [0005] The method route described in the literature is too long, the reaction is unstable, and quite a lot of reagents are expensive, so they cannot be used in industrial production. [0006] Farnesol, also known as farnesol, is a colorless sesquiterpene compound extracted from plants. Farnesol is poorly solu...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/02C07C29/14
Inventor 张芳江李成永
Owner SHANGHAI RECORD PHARM CO LTD