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Method for synthesizing beta-damascenone

A synthesis method and technology of turkone are applied in the field of synthesis of β-turkone, which can solve the problems of flammability and explosion, unfavorable safety production, easy damping of metal hydrides, etc., and achieves easy operation, high reaction yield, and decomposition reaction conditions. mild effect

Inactive Publication Date: 2013-02-20
SHANGHAI INST OF TECH +1
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  • 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

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  • Method for synthesizing beta-damascenone
  • Method for synthesizing beta-damascenone

Examples

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Embodiment 1

[0055] (1), Preparation of 2,6,6-trimethyl-1-(4-hydroxy-hept-1,6-dien-4-yl)-cyclohex-1-ene

[0056] In a 500-milliliter three-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a spherical condenser, add 28.8 grams (1.2 mol) of magnesium, a grain of iodine and anhydrous ether (the addition amount is 100 milliliters), and the stirring speed is controlled to be 120r / min, start to drip 84.2g (1.1mol) of allyl chloride and anhydrous ether (addition amount is 100ml) mixed solution, control the rate of dripping to 5g / min, complete the dropwise addition, keep the reaction for 1h. Then, 100 g of ethyl cyclogeranate (0.5 mol) with a content of 98% was started dropwise, and the drop rate was controlled to be 6 g / min. After the dropwise addition was completed, stirring was continued for 2 h. The reaction solution was poured into 1000 mL of saturated aqueous ammonium chloride solution, the organic layer was separated, and washed once with 500 mL of water until neut...

Embodiment 2

[0062] (1), Preparation of 2,6,6-trimethyl-1-(4-hydroxy-hept-1,6-dien-4-yl)-cyclohex-1-ene

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

Embodiment 3

[0069] (1), Preparation of 2,6,6-trimethyl-1-(4-hydroxy-hept-1,6-dien-4-yl)-cyclohex-1-ene

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

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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 method for synthesizing β-turkone. Background technique [0002] Cycloaliphatic ketones such as tuckenone and tuckenone, especially α- and β-tuckenone and β-tuckenone, are increasingly used in the fragrance and flavor industries. β-Turonicone has a strong and pleasant rose aroma and elegant aroma. 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. At present, the common synthesis method of β-turcoketone is to carry out Grignard reaction with ethyl cyclogeranate as raw material and allyl magnesium chloride to generate 2,6,6-trimethyl-1-(4-hydroxy-heptane-1, 6-Dien-4-yl)-cyclohex-1-ene, 2,6,6-trimethyl-1-(4-hydroxy-hept-1,6-dien-4-yl)-cyclohex -1-ene undergoes a decomposition reaction to generate 2,6,6-trimethyl-1-(but-3-enoyl)-cyclohex-1-ene, which is finally catalyzed by an acid...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/543C07C45/67
Inventor 李琼黄亚文卢星何锡敏
Owner SHANGHAI INST OF TECH
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