Convenient Method of Synthesizing Aryloxyalkyl Esters from Phenolic Esters Using Halogenated Alcohols

Xueyang Jiang; Junting Zhou; Yue Zhou; Haopeng Sun; Jian Xu; Feng Feng; Wei Qu

doi:10.3390/molecules23071715

Convenient Method of Synthesizing Aryloxyalkyl Esters from Phenolic Esters Using Halogenated Alcohols

Molecules. 2018 Jul 13;23(7):1715. doi: 10.3390/molecules23071715.

Authors

Xueyang Jiang¹, Junting Zhou², Yue Zhou³, Haopeng Sun⁴, Jian Xu⁵, Feng Feng^{6

7

8}, Wei Qu^{9

10}

Affiliations

¹ Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China. ajyang@stu.cpu.edu.cn.
² Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China. zhoujunting0920@163.com.
³ Department of Pharmacy Administration & Clinical Pharmacy, Peking University, Beijing 100191, China. yuezhouzhy@163.com.
⁴ Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China. sunhaopeng@163.com.
⁵ Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China. xujian201009@126.com.
⁶ Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China. fengfeng@cpu.edu.cn.
⁷ Key Laboratory of Biomedical Functional Materials, China Pharmaceutical University, Nanjing 210009, China. fengfeng@cpu.edu.cn.
⁸ Food and Drug Research Institute, Jiangsu Food & Pharmaceutical Science College, Huaian 223003, China. fengfeng@cpu.edu.cn.
⁹ Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China. popoqzh@126.com.
¹⁰ Key Laboratory of Biomedical Functional Materials, China Pharmaceutical University, Nanjing 210009, China. popoqzh@126.com.

Abstract

A facile one-pot synthetic method of building aryloxyalkyl esters was developed using various types of phenolic esters with halogenated alcohols. The ready availability of both starting materials, coupled with the required simple experimental technique, enables the current synthetic method of producing aryloxyalkyl esters in a fast and efficient way. It is noteworthy that acyl transfer was demonstrated in this reaction.

Keywords: acyl transfer; aryloxyalkyl esters; phenolic esters.

MeSH terms

Alcohols / chemistry*
Esters / chemical synthesis*
Esters / chemistry*
Hydrocarbons, Halogenated / chemistry*
Hydroxybenzoates / chemistry*

Substances

Alcohols
Esters
Hydrocarbons, Halogenated
Hydroxybenzoates
phenolic acid