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Synthetic method of 4-methyl-4-(cis-3-hexenyl)-4-butyrolactone

A synthesis method and hexenyl technology, applied in organic chemistry and other directions, can solve the problems of high cost, strong corrosiveness, and unsuitable for industrial production.

Active Publication Date: 2017-05-10
新乡市博源生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although 4-methyl-4-(cis-3-hexenyl)-4-butyrolactone is a spice and has the biological activity of inhibiting cytochrome 2A13, there are few literatures on its synthesis
This method has high cost and uses highly corrosive concentrated sulfuric acid, which is not suitable for industrial production

Method used

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  • Synthetic method of 4-methyl-4-(cis-3-hexenyl)-4-butyrolactone
  • Synthetic method of 4-methyl-4-(cis-3-hexenyl)-4-butyrolactone

Examples

Experimental program
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Effect test

Embodiment 1

[0015] (1) Synthesis of cis 1-chloro-3-hexene

[0016] Add leaf alcohol (100.0g, 1.0mol) and DMF (154mL) into a 500mL three-necked flask, stir well, cool the mixture to 5-10°C, slowly add thionyl chloride (125.0g, 1.05mol) dropwise, control The temperature of the reaction solution is lower than 25°C. After the dropwise addition was completed, the reaction was stirred for another 3 h, and the gas chromatography detection showed that the leaf alcohol content of the raw material was less than 0.5%, and the reaction was stopped. Distilled under reduced pressure to remove the solvent and thionyl chloride. The residue was washed with deionized water until neutral, and dried over anhydrous sodium sulfate to obtain cis-1-chloro-3-hexene (109.0 g, yield 92%) as a colorless liquid. 1 H NMR (400MHz, CDCl 3 )δ5.56-5.49(m,1H),5.36-5.29(m,1H),3.49(t,2H),2.53-2.47(m,2H),2.09-2.01(m,2H),0.96(t, 3H).GC-MS: m / z (relative intensity) 118 (M + ,39),41(100),55(86),69(77).

[0017] (2) Synthes...

Embodiment 2

[0025] (1) Synthesis of cis 1-chloro-3-hexene

[0026] Add leaf alcohol (200.0g, 2.0mol) and DMF (300mL) into a 1000mL three-necked flask, stir well, cool the mixture to 5-10°C, slowly add thionyl chloride (250.0g, 2.1mol) dropwise, control The temperature of the reaction solution is lower than 25°C. After the dropwise addition was completed, the reaction was stirred for another 5 h. Gas chromatography detection showed that the leaf alcohol content of the raw material was less than 0.5%, and the reaction was stopped. Distilled under reduced pressure to remove the solvent and thionyl chloride. The residue was washed with deionized water until neutral, and dried over anhydrous sodium sulfate to obtain cis-1-chloro-3-hexene (210.0 g, yield 89%) as a colorless oil. Product of cis-1-chloro-3-hexene 1 H NMR and GC-MS are the same as in Example 1.

[0027] (2) Synthesis of cis-5-hexen-2-one

[0028] Add THF (480mL) and magnesium chips (52.0g, 2.2mol) into a 1000mL three-necked f...

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Abstract

The invention belongs to the field of fine chemistry, and particularly relates to a synthetic method of 4-methyl-4-(cis-3-hexenyl)-4-butyrolactone. The method comprises the following steps: taking leaf alcohol as a starting material, enabling the leaf alcohol to react with thionyl chloride to generate cis-1-chloro-3-hexene, first reacting with metal magnesium to obtain a cis-3-hexenyl Grignard reagent, then reacting with acetyl chloride to generate cis-5-hexene-2-ketone, and then reacting with methyl propiolate in the presence of n-butyllithium to obtain cis-4-methy-4-hydroxyl-7-decene-2-acetylenic acid methyl ester, and finally directly performing the reaction cyclization with NaBH4 under the catalysis of CuCl to obtain the 4-methyl-4-(cis-3-hexenyl)-4-butyrolactone. The method is environment-friendly, low in cost and suitable for the industrialization production.

Description

technical field [0001] The invention belongs to the field of fine chemical industry, and in particular relates to a novel method for synthesizing 4-methyl-4-(cis-3-hexenyl)-4-butyrolactone suitable for industrial production. Background technique [0002] 4-Methyl-4-(cis-3-hexenyl)-4-butyrolactone (4-Methyl-4-(cis-3-hexenyl)-4-butyrolactone), that is, γ-methyl-γ -(cis-3-hexenyl)-butyrolactone, a synthetic lactone fragrance, can be used in household surface cleaning products, fabric softeners, air fresheners, oral care agents and deodorants and many other daily chemicals (Quellet, C.; Bieri, S. Patent GB2528480A, 2014, 7, 23). 4-Methyl-4-(cis-3-hexenyl)-4-butyrolactone was first synthesized by Stoll and Bolle, and the relationship between the structure and fragrance of this type of compound was studied (Stoll, M.; Bolle, P. Helv. Chim. Acta 1938, 21, 1547–1553.). Schilling's research shows that 4-methyl-4-(cis-3-hexenyl)-4-butyrolactone also has the biological activity of i...

Claims

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Application Information

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IPC IPC(8): C07D307/33
CPCC07D307/33
Inventor 张国清杨大志
Owner 新乡市博源生物科技有限公司
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