Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for synthesizing beta-damascenone

A synthesis method and a technology of turkone are applied in the synthesis field of β-turkone, can solve problems such as unfavorable safe production, metal hydrides are susceptible to moisture, flammable and explosive, and achieve easy operation, high reaction yield, and decomposition reaction conditions. mild effect

Inactive Publication Date: 2010-04-28
SHANGHAI INST OF TECH +1
View PDF0 Cites 10 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When 2,6,6-trimethyl-1-(4-hydroxy-hept-1,6-dien-4-yl)-cyclohex-1-ene is decomposed, metal hydride [Tetrahedron Letters, Vol.23, No.3, pp335-338, 1982], while metal hydrides are susceptible to moisture, flammable and explosive, so it is not conducive to safe 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 beta-damascenone
  • Method for synthesizing beta-damascenone
  • Method for synthesizing beta-damascenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] (1), the preparation of 2,6,6-trimethyl-1-(4-hydroxyl-hept-1,6-dien-4-yl)-cyclohex-1-ene

[0056] In the 500 milliliter three-neck flask equipped with agitator, thermometer, dropping funnel and spherical condenser, add 28.8 grams (1.2mol) magnesium, a grain of iodine and anhydrous ether (addition is 100 milliliters), control the stirring speed to 120r / min, start dropwise adding 84.2g (1.1mol) of allyl chloride and anhydrous ether (100ml addition) mixture, control the dropping rate at 5g / min, after the dropwise addition is complete, keep warm for 1h. Then, start to drop 100 g of ethyl geranate (0.5 mol) with a content of 98%, and control the dropping rate to 6 g / min. After the dropping is completed, continue stirring for 2 h. The reaction solution was poured into 1000 ml of saturated ammonium chloride aqueous solution, the organic layer was separated, and washed once with 500 ml of water until neutral. Recover the solvent under normal pressure and then distill under red...

Embodiment 2

[0062] (1), the preparation of 2,6,6-trimethyl-1-(4-hydroxyl-hept-1,6-dien-4-yl)-cyclohex-1-ene

[0063] In the 500 milliliter three-neck flask equipped with stirrer, thermometer, dropping funnel and spherical condenser, add 28.8 grams (1.2mol) magnesium, a grain of iodine and isopropyl ether (addition is 100 milliliters), control stirring speed to be 120r / min, start dropwise adding 84.2g (1.1mol) of allyl chloride and isopropyl ether (100ml addition) mixed solution, control the dropping rate at 5g / min, after dropwise addition, keep warm for 1h. Then, 100 g of ethyl geranate (0.5 mol) with a content of 98% was started to be added dropwise, and the dropping rate was controlled at 6 g / min. After the dropping was completed, stirring was continued for 3 h. The reaction solution was poured into 1000 ml of saturated ammonium chloride aqueous solution, the organic layer was separated, and washed once with 500 ml of water until neutral. Recover the solvent under normal pressure and t...

Embodiment 3

[0069] (1), the preparation of 2,6,6-trimethyl-1-(4-hydroxyl-hept-1,6-dien-4-yl)-cyclohex-1-ene

[0070] In the 500 milliliter three-neck flask equipped with agitator, thermometer, dropping funnel and spherical condenser, add 28.8 grams (1.2mol) magnesium, a grain of iodine and anhydrous ether (addition is 100 milliliters), control the stirring speed to 120r / min, start dropwise adding 84.2g (1.1mol) of allyl chloride and anhydrous ether (100ml addition) mixture, control the dropping rate at 5g / min, after the dropwise addition is complete, keep warm for 1h. Then, 100 g of ethyl geranate (0.5 mol) with a content of 98% was started to be added dropwise, and the dropping rate was controlled at 6 g / min. After the dropping was completed, stirring was continued for 3 h. The reaction solution was poured into 1000 ml of saturated ammonium chloride aqueous solution, the organic layer was separated, and washed once with 500 ml of water until neutral. Recover the solvent under normal pre...

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

No PUM Login to View More

Abstract

The invention discloses a method for synthesizing beta-damascenone, comprising three steps as follows: performing Grignard reaction on cyclized ethyl geranate and allylmagnesium chloride to obtain 2,6,6-trimethyl-1-(4-hydroxy-heptose-1,6-diene-4-base)-hexamethylene-1-alkene; decomposing 2,6,6-trimethyl-1-(4-hydroxy-heptose-1,6-diene-4-base)-hexamethylene-1-alkene to obtain 2,6,6-trimethyl-1-(butyl-3-acyl)-hexamethylene-1-alkene and 2,6,6-trimethyl-1(butyl-3-acyl)-hexamethylene-1-alkene; and performing isomerisation to obtain the beta-damascenone. The method for synthesizing beta-damascenone in the invention makes an improvement on decomposition reaction in a traditional method, uses easily obtained raw materials, has mild reaction conditions, safer and friendly process and high product yield. The product has intensive and pleasant rose fragrance, is an important raw material in daily health essence and is a very useful edible flavor.

Description

technical field [0001] The invention relates to a synthesis method of β-turkone. Background technique [0002] Cycloaliphatic ketones such as Turkone and Turkenone, especially α- and β-Turkenone and β-Turkenone, are increasingly used in the fragrance and flavor industries. β-Turkone has a strong and pleasant aroma of roses, which is elegant and elegant. It is not only an important raw material for daily chemical essence, but also a very useful edible spice. [0003] The chemical name of β-turkone is: 2,6,6-trimethyl-1-(but-2-enoyl)-cyclohex-1-ene. The common synthetic method of β-Turkone is that ethyl cyclogeranate is used as raw material to carry out Grignard reaction with allylmagnesium chloride to generate 2,6,6-trimethyl-1-(4-hydroxyl-hept-1, 6-dien-4-yl)-cyclohex-1-ene, 2,6,6-trimethyl-1-(4-hydroxy-hept-1,6-dien-4-yl)-cyclohexa -1-ene undergoes decomposition reaction to generate 2,6,6-trimethyl-1-(but-3-enoyl)-cyclohex-1-ene, and finally catalyzed by acid to 2,6,6-tr...

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
IPC IPC(8): C07C49/543C07C45/67
Inventor 李琼黄亚文卢星何锡敏
Owner SHANGHAI INST OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com