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

Article abstract of DOI:10.1055/s-1987-27832

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.