Synthesis of β-(3,4-Dihydroxyphenyl)-α-hydroxy Propionic Acid  Esters

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (9): 1466-1469. Previous Articles Next Articles

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β-(3,4-二羟基苯基)-α-羟基丙酸异丙酯/冰片酯合成研究

张群正*,a,b 董岩a 南叶飞c 蔡雪刁a 郑晓晖c

(a西安石油大学化学化工学院西安 710065)
(b陕西科技大学资源与环境学院西安 710021)
(c西北大学西部资源生物与现代生物技术省部共建教育部重点实验室西安 710069)

收稿日期:2008-09-02 修回日期:2009-03-10 发布日期:2009-12-30
通讯作者: 张群正

Synthesis of β-(3,4-Dihydroxyphenyl)-α-hydroxy Propionic Acid Esters

Zhang, Qunzheng ^*,a,b Dong, Yan ^a Nan, Yefei ^c Cai, Xuediao ^a Zheng, Xiaohui^c

(^a College of Chemistry and Chemical Engineering, Xi’an Shiyou University, Xi’an 710065)
(^b College of Resource and Environment, Shaanxi University of Science & Technology, Xi’an 710021)
(^c Key Laboratory of Resource Biology & Morden Biotechnoloby in Western China, Ministry of Education,
Nortwest University, Xi’an 710069)

Received:2008-09-02 Revised:2009-03-10 Published:2009-12-30
Contact: Zhang, Qunzheng

Abstract

β-(3,4-Dihydroxyphenyl)-α-hydroxy propionic acid isopropyl and propionic acid borneol esters have been synthesized by taking 3,4-dihydroxybenzaldehyde as a raw material, through its benzyl protection, darzens ring-oxidation, Lewis acid ring-opening, NaBH4 reduction, deprotection of the Bzl groups by catalytic hydropyrolysis. The structures of products have been characterized by the 1H NMR, 13C NMR, IR and MS techniques. The method contains the merits of easy manipulation and low toxcity.

Key words: β-(3,4-dihydroxyphenyl)-α-hydroxy propionic acid isopropyl ester, β-(3,4-dihydroxylphenyl)-α-hydroxy propionic acid borneol ester, super acid catalysis, esterification

Cite this article

Zhang, Qunzheng ^*,a,b Dong, Yan ^a Nan, Yefei ^c Cai, Xuediao ^a Zheng, Xiaohui^c. Synthesis of β-(3,4-Dihydroxyphenyl)-α-hydroxy Propionic Acid Esters[J]. Chin. J. Org. Chem., 2009, 29(9): 1466-1469.

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β-(3,4-二羟基苯基)-α-羟基丙酸异丙酯/冰片酯合成研究

Synthesis of β-(3,4-Dihydroxyphenyl)-α-hydroxy Propionic Acid Esters

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