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Preparation method for carbonic acid linalool oxide (pyran type and furan type) ester ethyl ester

A technology of linalool carbonate and oxide, which is applied in the field of preparation of ethyl linalool carbonate oxide, and achieves the effects of low production cost, convenient operation and low price

Inactive Publication Date: 2016-07-27
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Preparation method for carbonic acid linalool oxide (pyran type and furan type) ester ethyl ester

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preparation example Construction

[0021] The preparation method of linalool carbonate (pyran type and furan type) ethyl ester includes the following steps:

[0022] 1) In an ice-water bath, stir a solution consisting of 3,7-dimethyl-6,7-epoxy-2-octene-1-ol, dichloromethane and pyridine until uniform to obtain solution A, 10min Add the dichloromethane solution of ethyl chloroformate dropwise to the solution A while stirring. After the addition, continue to stir and react at room temperature for 10-20 hours. After the reaction is completed, the obtained reaction solution is hydrochloric acid with a concentration of 5% by mass. The aqueous solution adjusts the pH of the reaction solution to neutral to obtain a neutral reaction solution; among them, 3,7-dimethyl-6,7-epoxy-2-octene-1-ol, dichloromethane and pyridine are based on the amount of substance And volume ratio calculation, that is 3,7-dimethyl-6,7-epoxy-2-octene-1-ol: dichloromethane: pyridine is 1mol: 1.20~3.20L: 0.16~0.81L; chloroformic acid The concentrat...

Embodiment 1

[0034] A preparation method of linalool carbonate (pyran type and furan type) ethyl ester comprises the following steps:

[0035] (1) Place a mixed solution consisting of 2.11 grams (98.90%, 12.28mmol) 3,7-dimethyl-6,7-epoxy-2-octene-1-ol, 30ml dichloromethane and 8ml pyridine in In a three-necked flask, add dropwise 2.68 g of ethyl chloroformate in 10 ml of dichloromethane to the solution within 10 minutes at 0-5°C while stirring. After the addition, continue to stir and react at room temperature for 18 hours. The reaction is obtained after the reaction is complete Adjust the pH of the reaction solution to neutral with a hydrochloric acid aqueous solution with a concentration of 5% by mass;

[0036] (2) The reaction solution washed to neutral pH in step (1) was extracted with ether, and the resulting organic layer was washed with anhydrous MgSO 4 After drying and filtering with filter paper the next day, the filtrate obtained was evaporated and concentrated by a rotary evaporator ...

Embodiment 2

[0044] A preparation method of linalool carbonate (pyran type and furan type) ethyl ester comprises the following steps:

[0045] (1) Put 2.02 grams (98.90%, 11.75mmol) 3,7-dimethyl-6,7-epoxy-2-octene-1-ol, 30ml dichloromethane and 10ml pyridine in a mixed solution In a three-necked flask, add 2.55 g of ethyl chloroformate in 10 ml of dichloromethane to the solution in 10 minutes at 0-5°C while stirring. After the addition, continue to stir and react at room temperature for 18 hours. The reaction is obtained after the reaction is complete Adjust the pH of the reaction solution to neutral with a hydrochloric acid aqueous solution with a concentration of 5% by mass;

[0046] (2) The reaction solution washed to neutral pH in step (1) was extracted with ether, and the resulting organic layer was washed with anhydrous MgSO 4 After drying and filtering with filter paper the next day, the filtrate obtained was evaporated and concentrated by a rotary evaporator to obtain 2.44g crude produc...

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Abstract

The invention relates to a preparation method for carbonic acid linalool oxide (pyran type and furan type) ester ethyl ester.The method comprises the following steps that 1, a solution composed of 3,7-dimethyl-6,7-epoxy-2-octylene-1-ol, dichloromethane and pyridine is stirred to be uniform, a dichloromethane solution of ethyl chloroformate is added into the solution dropwisely, after a stirring reaction is finished, a hydrochloric acid water solution is used for adjusting a reaction solution pH to be neutral; 2, the neutral reaction is extracted through diethyl ether, an obtained organic layer is dried through anhydrous MgSO4, filtering is performed the next day and then evaporation and concentration are performed to obtain a carbonic acid linalool oxide (pyran type and furan type) ester ethyl ester product; 3, the crude product is separated through a silica gel column, a mixed solvent composed of petroleum ether and ethyl acetate is used as an eluting agent for elution, rotary evaporation is performed to remove petroleum ether and ethyl acetate to obtain the carbonic acid linalool oxide (pyran type and furan type) ester ethyl ester.Compared with the prior art, raw materials are easy to obtain, the preparation process is simple, operation is convenient, the yield is high, and the preparation method is suitable for industrial production.

Description

[Technical Field] [0001] The invention relates to the technical field of preparation methods of carbonate monoterpene alcohol ester perfume precursors, in particular to a preparation method of linalool carbonate (pyran type and furan type) ester ethyl ester. [Background technique] [0002] Linalool carbonate (pyran type and furan type) ethyl ester is a monoterpene carbonate. Linalool oxide (pyran type and furan type) ethyl esters exist in both cis and trans forms. They are widely found in orange leaf oil, rose oil, lavender oil and various plant essential oils. It is a very useful fragrance precursor. Linalool oxide (pyran type and furan type) ethyl ester slowly releases a special aroma under the action of external factors such as heating, pressure, and mechanical friction. Fragrance precursors have a wide range of applications in the fragrance, food and cosmetic industries. [0003] Since Bouque and Bride discovered geranyl-β-D-pyranyl glucoside in plants in 1913, research at ho...

Claims

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Application Information

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IPC IPC(8): C07D307/16C07D309/10
CPCC07D307/16C07D309/10
Inventor 杨始刚秦婷施子楠
Owner SHANGHAI INST OF TECH
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