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Preparation method of hydratropic aldehyde

A technology of Solanum aldehyde and Solanum aldehyde sulfonate, which is applied in the preparation of heterocyclic compounds, the separation/purification of carbonyl compounds, organic chemistry, etc., can solve the problems of difficult availability of raw materials and restrictions on industrial use, and achieve easy industrialization , low cost, and simple reaction steps

Inactive Publication Date: 2013-09-18
NANTONG CHENGXIN AMINO ACID
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the method has the advantages of low cost, mild reaction, and few reaction steps, catalysts, acetic anhydride and oxidizing agents are used in the process, and the safety of the process, the friendliness to the environment, and the cost of the process restrict industrial use.
Shi Zhen et al. (Shi Zhen, Chemical Journal of Chinese Universities, 2001, 22, 1352; CN101134718A) added benzimidazolium salt and α-phenylethylmagnesium bromide to generate benzimidazolidine intermediate, and then under acidic conditions Solanum aldehyde can be obtained by hydrolysis. This method has the advantages of high yield, good product purity, and easy operation. However, the raw materials of this method are not easy to obtain, and a large amount of research work needs to be carried out if it is really applied to actual production.

Method used

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  • Preparation method of hydratropic aldehyde
  • Preparation method of hydratropic aldehyde
  • Preparation method of hydratropic aldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Weigh 5000g of 20% sodium methoxide into a 10L reaction flask, control the temperature down to 20°C, add 1200g of acetophenone into a 10L reaction flask, slowly add 1.5Kg of methyl chloroacetate dropwise, after 1h of dropwise addition, stir for 2h, The results showed that the reaction was basically complete. Ethanol is removed, and rectification under reduced pressure is obtained to obtain 3-methyl-3-phenylglycidic acid methyl ester with a content ≥ 98%, and the yield is 70-80%.

[0032] In a three-necked flask equipped with a thermometer, stirring, and 10L, add 1kg of the above-mentioned 3-methyl-3-phenyl glycidic acid methyl ester, 1L of 20% aqueous sodium hydroxide solution, stir the reaction, and follow the reaction by chromatography. Until the glyceride is completely converted, the reaction time is about 4 hours and the 3-methyl-3-phenylglycidyl sodium salt is obtained by filtration with a yield of 90-100%.

[0033] Add 1000 g of the above-prepared 3-methyl-3-phen...

Embodiment 2

[0037] Weigh 3000g of 20% sodium ethoxide into a 10L reaction flask, control the temperature down to 10°C, add 1500g of acetophenone into a 10L reaction flask, slowly add 1.5Kg of ethyl chloroacetate dropwise, after 1h of dropwise addition, stir for 2h, Sent to GC for detection, the results showed that the reaction was basically complete. Ethanol is removed, and 3-methyl-3-phenyl glycidic acid ethyl ester with a content ≥ 98% is obtained by rectification under reduced pressure, and the yield is 70-80%.

[0038] In a three-necked flask equipped with a thermometer, stirring, and 10L, add 1kg of the above-mentioned 3-methyl-3-phenyl glycidic acid ethyl ester, 1L of 20% aqueous sodium hydroxide solution, stir the reaction, and follow the reaction by chromatography. Until the ethyl glycerate is completely converted, the reaction time is about 10 hours and the 3-methyl-3-phenylglycidyl sodium salt is obtained by filtration with a yield of 90-100%.

[0039] In a three-neck flask equip...

Embodiment 3

[0043] Weigh 3600g of 20% sodium isopropoxide into a 10L reaction flask, control the temperature down to 40°C, add 1200g of acetophenone into a 10L reaction flask, slowly add 2.4Kg of ethyl chloroacetate dropwise, after 1 hour of dropwise addition, stir 5h, sent for detection, the results showed that the reaction was basically complete. Remove ethanol, rectify under reduced pressure (1mmHg) to obtain 3-methyl-3-phenyl glycidic acid ethyl ester with a content ≥ 98%, and the yield is 70-80%.

[0044] In a three-necked flask equipped with a thermometer, stirring, and 10L, add 1kg of the above-mentioned 3-methyl-3-phenyl glycidic acid ethyl ester, 1L of 20% aqueous sodium hydroxide solution, stir the reaction, and follow the reaction by chromatography. Until the ethyl glycerate was completely converted, the reaction time was about 24 hours and the sodium salt of 3-methyl-3-phenylglycidyl was obtained by filtration with a yield of 90-100%.

[0045] Add 1 kg of the above-prepared 3...

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Abstract

The invention relates to a preparation method of hydratropic aldehyde. The method comprises the following steps: performing condensation reaction on acetophenone and halogenated acetate used as raw materials to obtain 3-methyl-3-phenyl glycidic ester, hydrolyzing in an alkali water solution to obtain 3-methyl-3-phenyl glycerate, performing pH regulation and acidification, performing isomerism reaction to obtain a hydratropic aldehyde rough product, reacting with hydrosulphite to obtain hydratropic aldehyde sulfonate, adding alkali to neutralize to obtain an organic layer, separating, washing and drying to obtain the target product hydratropic aldehyde.

Description

technical field [0001] The technology of the invention relates to the field of chemical technology, in particular to the field of perfume synthesis. Background technique [0002] The chemical name of Solanum aldehyde is 2-phenylpropanal, the English name is: Hydratropic aldehyde or 2-Phenyl propional aldehyde, the CAS registration number is [93-53-8], and the chemical structural formula is: [0003] [0004] Solanal is a precious spice and an important chemical raw material, widely used in spices, medicine, fuel and pesticide industries. During the industrial production method of Solanum aldehyde, acetophenone and ethyl chloroacetate are used as raw materials, according to the Darzens method (referring to aldehyde or ketone with α-halogenated carboxylate under the action of strong base <such as sodium amide, sodium alkoxide> Reaction, the reaction to generate α, β-epoxy ester. Named after the discoverer August George Dakin <1867-1954>. The product α, β-epoxy ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/228C07C45/58C07C45/78
Inventor 邢将军许刘华曹铭
Owner NANTONG CHENGXIN AMINO ACID
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