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Vol. 26 No. 23 (2014)

Copyright (c) 2014 Zhu-Ping Xiao*, Wei Wei, Shen Huang, Xiao-Yi Lin, Bin Peng, Xu-Dong Wang, Lei Zhang

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Selective Acylation of Phenols in Boron Trifluoride Diethyl Etherate Solution and the Mechanistic Implication

https://doi.org/10.14233/ajchem.2014.17019
Zhu-Ping Xiao*
College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P.R. China *Corresponding author: Tel/Fax: + 86 74 8563911; E-mail: xiaozhuping2005@163.com
Wei Wei
College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P.R. China *Corresponding author: Tel/Fax: + 86 74 8563911; E-mail: xiaozhuping2005@163.com
Shen Huang
College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P.R. China *Corresponding author: Tel/Fax: + 86 74 8563911; E-mail: xiaozhuping2005@163.com
Xiao-Yi Lin
College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P.R. China *Corresponding author: Tel/Fax: + 86 74 8563911; E-mail: xiaozhuping2005@163.com
Bin Peng
College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P.R. China *Corresponding author: Tel/Fax: + 86 74 8563911; E-mail: xiaozhuping2005@163.com
Xu-Dong Wang
College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P.R. China *Corresponding author: Tel/Fax: + 86 74 8563911; E-mail: xiaozhuping2005@163.com
Lei Zhang
College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P.R. China *Corresponding author: Tel/Fax: + 86 74 8563911; E-mail: xiaozhuping2005@163.com

Corresponding Author(s) : Zhu-Ping Xiao*

Asian Journal of Chemistry, Vol. 26 No. 23 (2014)

Abstract

In the presence of boron trifluoride diethyl etherate (BF3·OEt2), direct acylation of phenols with free carboxylic acid is chemoselective and regioselective and no demethylation, if any, was observed. The para-directing effect of BF3·OEt2 is attributed to the large steric hindrance of the boron trifluoride-phenolic hydroxyl group complex, which blocks the ortho-acylation from occurrence. Microwave irradiation could not change the regioselectivity of BF3·OEt2 except the reaction time being greatly shortened.

Keywords

Regioselectivity Direct acylation of phenol Boron trifluoride diethyl ehterate.
Xiao*, Z.-P., Wei, W., Huang, S., Lin, X.-Y., Peng, B., Wang, X.-D., & Zhang, L. (2014). Selective Acylation of Phenols in Boron Trifluoride Diethyl Etherate Solution and the Mechanistic Implication. Asian Journal of Chemistry, 26(23), 8039–8042. https://doi.org/10.14233/ajchem.2014.17019
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