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Method for preparing alkyl furanone by low-temperature condensation method

A technology of alkyl furanone and condensation method, applied in organic chemistry and other directions, can solve the problems of long process cycle, high toxicity of raw materials, complicated process, etc., and achieve the effects of short process cycle, ideal yield and easy availability of raw materials

Inactive Publication Date: 2009-04-01
TIANJIN CHEM REAGENT RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But all there is various shortcoming in above-mentioned method, and method (1) technique is complicated, and yield is low; complex

Method used

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  • Method for preparing alkyl furanone by low-temperature condensation method
  • Method for preparing alkyl furanone by low-temperature condensation method
  • Method for preparing alkyl furanone by low-temperature condensation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 1. Preparation of tert-butyl sodium acetoacetate

[0030] Add 3000ml of anhydrous diethyl ether in the three-necked flask, then put 150 grams (6.52mol) of sodium metal, then dropwise add 1135 grams (7.18mol) of tert-butyl acetoacetate, the rate of addition is until the diethyl ether refluxes, and maintains reflux for 3 Hours, the metal sodium was fully reacted, and the reaction product was white and thick sodium tert-butyl acetoacetate.

[0031] 2. Preparation of furan ring

[0032] In a three-necked flask equipped with a thermometer, mechanical stirring, and a dropping funnel, add white thick tert-butyl sodium acetoacetate, and add 600 grams (3.24mol) of α-bromobutyryl chloride dropwise to tert-butyl sodium acetoacetate. In the ester, the temperature of the reactant is controlled at -10°C during the dropwise addition process, and the temperature is maintained for 1 hour after the addition, and then placed at room temperature for 12 hours, and 900ml of water is added t...

Embodiment 2

[0038] 1. Preparation of tert-butyl sodium acetoacetate

[0039] Add 1500ml of anhydrous ether in the three-necked flask, then put 100 grams (4.35mol) of sodium metal, and then dropwise add 757 grams (4.79mol) of tert-butyl acetoacetate, the rate of addition is until the ether is refluxed, and the reflux is maintained for 5 minutes after adding. Hours, the metal sodium was fully reacted, and the reaction product was white and thick sodium tert-butyl acetoacetate.

[0040] 2. Preparation of furan ring

[0041] In a three-necked flask equipped with mechanical stirring, a thermometer, and a dropping funnel, add white thick tert-butyl sodium acetoacetate, and add 402 grams (2.17mol) of α-bromobutyryl chloride dropwise to tert-butyl sodium acetoacetate. In the butyl ester, the temperature of the reactant is controlled at -12°C during the dropwise addition process, and the reaction is maintained at this temperature for 2 hours after the addition, and then placed at room temperature...

Embodiment 3

[0047] 1. Preparation of tert-butyl sodium acetoacetate

[0048] Add 3000ml of anhydrous ether in the there-necked flask, then put 125 grams (5.43mol) of sodium metal, then dropwise add 945 grams (5.98mol) of tert-butyl acetoacetate, the rate of addition is so far that the ether is refluxed, and the reflux is maintained for 4 hours after adding. Hours, the metal sodium was fully reacted, and the reaction product was white and thick sodium tert-butyl acetoacetate.

[0049] 2. Preparation of furan ring

[0050] In a three-necked flask equipped with a thermometer, mechanical stirring, and a dropping funnel, add white thick tert-butyl sodium acetoacetate, and add 500 grams (2.7mol) of α-bromobutyryl chloride dropwise to tert-butyl sodium acetoacetate. In the ester, the temperature of the reactant is controlled at -11°C during the dropwise addition process, and the temperature is maintained for 1 hour after the addition, and then placed at room temperature for 10 hours, and 1000ml o...

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Abstract

The invention relates to a method adopting a low-temperature condensation method to prepare alkyl furanone. The method firstly adopts active hydrogen atoms in the t-butyl acetoacetate to react with sodium metal to prepare sodio-t-butyl acetoacetate; then the sodio-t-butyl acetoacetate and alpha-bromo-butyryl-chloride are condensed under the low temperature to form the furan nucleus with the alkyl, then the furan nucleus is decomposed under decompression and finally the outcome of decomposing under decompression is oxidated to prepare the required product. Compared with the prior art, the method has more advantages that not only the material is more available, the process cycle is comparatively short, the operation is easy and the yield is satisfying, but also the obtained alkyl furanone is better in color, odor and flavor, and the like.

Description

technical field [0001] The invention relates to a method for preparing an organic compound, in particular to a method for preparing an alkyl furanone by a low-temperature condensation method. Background technique [0002] Alkyl furanones with sauce-flavored and fruity-flavored flavors are widely used food spices and occupy a very important position in the flavoring industry. 4-Hydroxy-2(5)-methyl-5(2)-ethyl-3(2H)furanone (4-Hydroxy-2(5)-Methyl-5(2)- Ethyl-3(2H)-Furanone, hereinafter referred to as HEMF), is more representative because of its strong sauce aroma and pineapple aroma. HEMF can be used not only as a perfume, but also as an intermediate, combined with sulfides and heterocyclic compounds, and then transformed into substances that can emit various fragrances. There are many synthetic methods of HEMF, and the commonly used methods are: (1). Use ozone to oxidize 3-ethylene-2,5-diol and then further cyclize to obtain HEMF; (2). Utilize crotonoyl nitrile and ethyl lac...

Claims

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Application Information

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IPC IPC(8): C07D307/60
Inventor 石开丁
Owner TIANJIN CHEM REAGENT RES INST
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