Preparation method of alkyl furanone

A technology of alkyl furanone and mixed solution, applied in the direction of organic chemistry, can solve the problems of highly toxic raw materials, complicated process, low yield, etc., and achieve the effect of short preparation process cycle, easy access to raw materials, and ideal yield

Inactive Publication Date: 2010-05-26
TIANJIN CHEM REAGENT RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many existing methods for synthesizing HDMF, but there are certain disadvantages, such as: (1). The further cyclization of 3-ethylene-2,5-diol can be used to oxidize ozone to obtain HDMF. (2). Utilize crotonoyl nitrile and ethyl lactate to prepare HDMF chlorinated condensation method un...

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] (1). Add 3000ml of anhydrous diethyl ether in a three-necked flask, then put 100g of sodium metal into it, and then add 757g of tert-butyl acetoacetate dropwise. Fully react to obtain the mixed liquid A, and the reaction product is white thick sodium tert-butyl acetoacetate.

[0021] (2). Add mixture A to a three-necked flask equipped with a thermometer, a mechanical stirring device, and a dropping funnel, and add 371 g of α-bromopropionyl chloride dropwise to tert-butyl sodium acetoacetate, and control the reaction temperature during the dropwise addition 12°C, maintain this temperature for 2 hours after adding, then stand at room temperature for 10 hours, add 1100ml of water to separate the product, wash the separated organic phase with water to separate the water layer, and extract the water layer with 1000ml of ether for 2 hours, combine The organic phase was dried with 50 g of anhydrous magnesium sulfate to obtain a mixed liquid B.

[0022] (3). After distilling o...

Embodiment 2

[0025] (1). Add 3000ml of anhydrous diethyl ether in a three-necked flask, then put 125g of sodium metal, then dropwise add 945g of tert-butyl acetoacetate, the rate of addition is until the ether is refluxed, and maintain reflux for 4 hours after the addition is completed, so that the sodium metal Fully react to obtain the mixed liquid A, and the reaction product is white thick sodium tert-butyl acetoacetate.

[0026] (2). Add mixture A to a three-neck flask equipped with a thermometer, a mechanical stirring device, and a dropping funnel, and add 461.7 g of α-bromopropionyl chloride dropwise to tert-butyl sodium acetoacetate, and control the reaction during the dropwise addition The temperature was 13°C, and the temperature was maintained for 1 hour after the addition, and then stood at room temperature for 10 hours, and 1000ml of water was added to separate the product, and the separated organic phase was washed with water, and the aqueous layer was extracted with 1000ml of e...

Embodiment 3

[0030] (1). Add 3000ml of anhydrous diethyl ether in a three-necked flask, then put 150g of sodium metal, and then add 1125g of tert-butyl acetoacetate dropwise. Fully react to obtain the mixed liquid A, and the reaction product is white thick sodium tert-butyl acetoacetate.

[0031] (2). Add mixture A to a three-necked flask equipped with a thermometer, a mechanical stirring device, and a dropping funnel, and add 554 g of α-bromopropionyl chloride dropwise to tert-butyl sodium acetoacetate, and control the reaction temperature during the dropwise addition 15°C, maintain this temperature for 1 hour after adding, then stand at room temperature for 12 hours, add 900ml of water to separate the product, wash the separated organic phase with water, extract the aqueous layer with 1000ml of ether for 1 hour, combine the organic phases, Drying was performed with 50 g of anhydrous magnesium sulfate to obtain a mixed liquid B.

[0032] (3). After distilling off the diethyl ether in the...

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PUM

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Abstract

The invention relates to a preparation method of alkyl furanone. The preparation steps are as follows: dripping acetyl tert-butyl acetate into absolute aether containing sodium metal until aether reflow, maintaining reflux after finishing dripping to obtain mixed solution A; dripping alpha-bromo-propionyl chloride into mixed solution A at 12-15 DEG C, maintaining the temperature after finishing dripping, standing at room temperature, precipitating the organic phase and washing with water, extracting the aqueous layer with aether, merging the organic phase and drying to obtain mixed solution B; evaporating mixed solution B out of aether, carrying out reduced pressure reaction on the residual liquid to obtain mixed solution C; and refining mixed solution C, blending with water, regulating pH value with sodium hydroxide solution to 7.9-8, adding hydrogen peroxide, regulating pH value of the product with hydrochloric acid solution to 1-2, extracting with aether, drying extract, removing aether and carrying out reduced pressure evaporation to obtain pale yellow oil-solid mixture, i.e. finished product of alkyl furanone. The preparation method has short technique period, simple operation, satisfactory yield, and good color, scent and flavor of the finished product.

Description

technical field [0001] The invention belongs to the field of organic compounds, in particular to a preparation method of alkyl furanone. Background technique [0002] Alkyl furanone is a widely used food spice, which has a strong sauce and fruity aroma, and occupies an important position in the flavoring industry. 4-hydroxy-2,5-dimethyl-3(2H)-furanone (4-Hydroxy-2,5-dimethyl-3(2H)-Furanone, hereinafter referred to as HDMF) in alkyl furanone spices, because of its strong The sauce aroma and pineapple aroma are more representative. HDMF can be used not only as a spice, but also as an intermediate and combined with a sulfide heterocyclic compound to transform into a substance that can emit various aromas. There are many existing methods for synthesizing HDMF, but there are certain disadvantages, such as: (1). The further cyclization of 3-ethylene-2,5-diol can be used to oxidize ozone to obtain HDMF. (2). Utilize crotonoyl nitrile and ethyl lactate to prepare HDMF chlorination...

Claims

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Application Information

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IPC IPC(8): C07D307/33
Inventor 石开丁
Owner TIANJIN CHEM REAGENT RES INST
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