Preparation of $\alpha $-hydroxyphenylacetic acid with cyclodextrins as an effective phase-transfer catalyst and its reaction mechanism

Authors

BING REN TIAN
RUI XIA ZHANG
HUI MIN CHU
QING HUANG
ZHI ZhONG WANG

Abstract

An effective procedure for the synthesis of $\alpha $-hydroxyphenylacetic acid with cyclodextrin (CD) catalysts was developed. The phase-transfer catalyst types, catalyst loadings, reaction times, reaction temperatures, and substrate molar ratios were investigated to optimize the reaction conditions. In addition, the factors that affect the reaction were studied, and the relationship between benzaldehyde and $\beta $-cyclodextrin ($\beta $-CD) was analyzed through 2D-ROESY. The equilibrium constant when $\beta $-CD was used as the catalyst was calculated. The results indicated that $\beta $-CD is the optimal catalyst for the reported reaction (yield: 69.08%). Furthermore, the mechanism underlying the reported reaction was proposed.

DOI

10.3906/kim-1809-37

Keywords

Yclodextrin, benzaldehyde, $\alpha $-hydroxyphenylacetic acid, equilibrium constant, reaction mechanism

First Page

359

Last Page

368

Recommended Citation

TIAN, BING REN; ZHANG, RUI XIA; CHU, HUI MIN; HUANG, QING; and WANG, ZHI ZhONG (2019) "Preparation of $\alpha $-hydroxyphenylacetic acid with cyclodextrins as an effective phase-transfer catalyst and its reaction mechanism," Turkish Journal of Chemistry: Vol. 43: No. 1, Article 29. https://doi.org/10.3906/kim-1809-37
Available at: https://journals.tubitak.gov.tr/chem/vol43/iss1/29