Standard Article

Orton Rearrangement

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr471

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Orton Rearrangement. Comprehensive Organic Name Reactions and Reagents. 471:2092–2096.

Publication History

  1. Published Online: 15 SEP 2010

Abstract

This reaction is the rearrangement of an N-chloro acyl anilide into an N-acyl p-chloroanilide in the presence of an acid such as HCl and is generally known as the Orton rearrangement. This reaction proceed via a multistep processes and is promoted simultaneously by proton (i.e., H+) and chloride. It has been found that both solvent composition and substrate influence this rearrangement. In addition, the Orton rearrangement can be triggered by a Lewis acid as well as by light. Furthermore, it has been reported that the chlorination of acyl anilide from chlorine can proceed by two paths and the ortho/para ratio of isomers increase when the solvent viscosity is increased. This reaction is useful for the preparation of para-halo anilides.

Keywords:

  • N-acyl p-chloroanilide;
  • Lewis acid;
  • hypochlorous acid;
  • N-acetonaphthalide