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Production of 1,2-diene methyl butyrate

A technology for the production of methyl diene butyrate, which is applied in 1, can solve the problems of increased production cost, large amount of solvent, and high price, and achieve the effects of improved production efficiency, simple reaction conditions, and short reaction cycle

Inactive Publication Date: 2005-02-23
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, all solvents are required to be anhydrous in the literature, and nitrogen protection is required during the reaction, which is very difficult for industrial production; The by-product of phosphine is expensive n-pentane, which increases the production cost
Subsequently, diethyl ether, petroleum ether and other solvents were chosen to replace n-pentane, and it was found that because the solvent has a certain solubility to triphenylphosphine oxide, the post-processing leaching and filtration needs to be repeated several times, and the large amount of solvent and the long working time also increased the production cost.

Method used

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  • Production of 1,2-diene methyl butyrate
  • Production of 1,2-diene methyl butyrate
  • Production of 1,2-diene methyl butyrate

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Dissolve 1000 g (3.82 mol) of triphenylphosphine in 3000 ml of benzene and place it in a 5 L reaction flask. At room temperature, 362 ml (3.82 mol) of methyl α-bromoacetate was slowly added dropwise, and reacted overnight at room temperature, and a large amount of white solid precipitated out. After filtration, the solid was washed with ether and dissolved in warm water. After complete dissolution, basify with 2N aqueous sodium hydroxide solution, a large amount of white solids precipitate out of the solution, filter after cooling, wash the solids with water, and dry in the air. 1223 g of white solid methoxycarbonylmethylene triphenylphosphine were obtained, yield: 95.9%.

[0022] Dissolve 334 grams (1.0 mol) of methoxycarbonylmethylene triphenylphosphine in 1100 ml of dichloromethane and 169 ml of triethylamine (1.2 mol), and add 86 ml (1.2 mol) of acetyl chloride and 50 ml of dichloromethane dropwise under reduced pressure. The mixed solution of methane was added in...

Embodiment 2

[0025] The preparation method of methoxycarbonylmethylene triphenylphosphine is the same as Example 1.

[0026] Dissolve 167 grams (0.5 mol) of methoxycarbonylmethylene triphenylphosphine in 700 ml of dichloromethane and 140 ml of triethylamine (1.0 mol), and add 37 ml (0.5 mol) of acetyl chloride and 150 ml of dichloromethane dropwise at room temperature After the addition, the reaction was continued at room temperature for 10 hours. After the reaction stopped, the oil pump decompressed to extract the product solution, the obtained solution was concentrated, and the water pump decompressed to distill the product to obtain 20 g of colorless liquid with a yield of 41%. Additional products 1 HNMR spectrum, figure 2 It shows that while containing the product 1,2-diene butanoic acid methyl ester, another 2-chloro-2-butenoic acid methyl ester, acetic acid and acetic anhydride impurities are generated.

Embodiment 3

[0028] The preparation method of methoxycarbonylmethylene triphenylphosphine is the same as Example 1.

[0029]3.4 grams (0.01mol) of methoxycarbonyl methylene triphenylphosphine are dissolved in the dichloromethane that 40ml phosphorus pentoxide is processed, and the triethylamine ( 0.02mol) and 10ml of dichloromethane mixed solution was stirred for 10 minutes, and then a mixed solution of redistilled acetyl chloride 1.1ml (0.01mol) and 10ml of dichloromethane was added dropwise. After the addition was complete, the reaction was continued at room temperature for 0.5 hours. After the reaction stopped, the obtained reaction mother liquor was concentrated, washed with petroleum ether for 4 times, filtered and combined to concentrate the organic layer, and the product was distilled off under reduced pressure by a water pump to obtain 0.5 g of light yellow liquid with a yield of 51%. Additional products 1 HNMR spectrum, see image 3 .

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Abstract

This invention relates to production of 1,2-diols methyl butyrate. After two procedures, the 1,2-diols methyl butyrate is produced by: using alpha-bromized methyl acetate and triphenyl phosphine as raw materials, generating phosphine ylide-methoxycarbonyl triphenyl phosphine, then using the phosphine ylide and acetyl chlorine to produce the 1,2-diols methyl butyrate.

Description

technical field [0001] This patent introduces the production method of methyl 1,2-diene butyrate, so that it can produce high-purity methyl 1,2-diene butyrate under conventional conditions using general reagents, so as to achieve the goal of industrial production skills requirement. Background technique [0002] Methyl 1,2-dienebutyrate is a kind of chemical intermediate with wide application. It is easily cyclized under the attack of different electrophiles to generate a biologically active chemical intermediate furanone, that is, γ-butenolide ring compound, and γ-butenolide ring compound is used in the synthesis of some natural products. Very wide range of uses [a) J.Am.Chem.Soc.1979, 1544; b) J.Org.Chem.1982, 1221]; in addition, methyl 1,2-diene butyrate is easily formed by addition of halogenated compounds A multi-substituted olefin, which is difficult to synthesize directly in conventional chemical preparation, has extremely high scientific research value. Therefore,...

Claims

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Application Information

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IPC IPC(8): C07C67/30C07C69/587
Inventor 麻生明金鑫蔡杨君
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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