Download PDF
Synthesis 1987; 1987(1): 35-37
DOI: 10.1055/s-1987-27832
communication
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

A New Method for the Synthesis of tert-Alkyl Chlorides from tert-Alcohols

David Crich* , Simon M. Fortt
  • *Department of Chemistry, University College London, 20 Gordon Street, London, WC1H OAJ, UK
Further Information

Publication History

Publication Date:
20 August 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Tert-Alkyl chlorides 5 are prepared in good yield from the corresponding alcohols 1 in a facile two step synthesis. The method involves treatment of the corresponding crude oxalyl monochloride alkyl ester 2 with N-hydroxy-pyridine-2-thione sodium salt 3 in tetrachloromethane at reflux to give the bright yellow N-(alkoxyoxalyloxy) pyridine-2-thiones 4 which undergo decomposition to the chlorides 5 in good yield. The reaction is conveniently monitored by the loss of colour from the mixed anhydride.