Syntheses of Capsaicin and (E)-4-Hydroxy-3-methoxybenzyl-8-methylnon-6-enoate

Chem. J. Chinese Universities

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Syntheses of Capsaicin and (E)-4-Hydroxy-3-methoxybenzyl-8-methylnon-6-enoate

YANG Yan, JIN Yong-Sheng, DONG Zhen-Xiu, HU Hong-Gang, YU Shi-Chong, WU Qiu-Ye*

Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received:2006-09-14 Revised:1900-01-01 Online:2007-07-10 Published:2007-07-10
Contact: WU Qiu-Ye

Abstract

Abstract:

Capsaicin and (E)-4-hydroxy-3-methoxybenzyl-8-methylnon-6-enoate were important intermediate of medicine. This research proposed a new method for synthesizing them from 6-bromohexanoic ester by Wittig reaction to give (Z)-8-methyl-6-nonenoic acid(4), then treated by nitrous acid and NaNO₂ to induce Z→E isomerization reaction of the carbon-carbon double bond, then followed by condensation reaction to give product in an overall yield of 31%. The method is more convenient than traditional methods.

Key words: Capsaicin, (E)-4-hydroxy-3-methoxybenzyl-8-methylnon-6-enoate, Wittig reaction

CLC Number:

O621

TrendMD:

YANG Yan, JIN Yong-Sheng, DONG Zhen-Xiu, HU Hong-Gang, YU Shi-Chong, WU Qiu-Ye*. Syntheses of Capsaicin and (E)-4-Hydroxy-3-methoxybenzyl-8-methylnon-6-enoate[J]. Chem. J. Chinese Universities, doi: .

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Syntheses of Capsaicin and (E)-4-Hydroxy-3-methoxybenzyl-8-methylnon-6-enoate

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