Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

A Facile Preparation of α-Aryl Carboxylic Acid via One-Flow Arndt–Eistert Synthesis

Shinichiro Fuse A B C , Yuma Otake A , Yuto Mifune A and Hiroshi Tanaka A
+ Author Affiliations
- Author Affiliations

A Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo 152-8552, Japan.

B Current address: Chemical Resources Laboratory, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan.

C Corresponding author. Email: sfuse@res.titech.ac.jp

Australian Journal of Chemistry 68(11) 1657-1661 https://doi.org/10.1071/CH15342
Submitted: 10 June 2015  Accepted: 14 July 2015   Published: 11 August 2015

Abstract

An efficient, one-flow Arndt–Eistert synthesis was demonstrated. A sequence of acid chloride formation–nucleophilic acyl substitution–Wolff rearrangement–nucleophilic addition was performed in a microflow system without isolating any intermediates, which included a potentially explosive compound. The microflow system was made from simple, inexpensive, and readily available instruments and tubes. α-Aryl esters 2a and 2b were prepared in yields of 33 and 23 % (three steps) respectively.


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