Mechanistic investigation of an anomalous anchimeric assistance in the acid hydrolysis of the ether linkage. Part 4

Kinetic investigation of the acid hydrolysis of N-(methoxyprop-2-yl)benzanilide (1) was performed in 8.84 M HCl and/or DCl at 75.1°C. The formation of 2-(N-phenylamino)propanol (4) was explained and the mechanism, involving an initial ether cleavage anchimerically assisted by the amide group, was clarified. The overall process evolves through three steps involving two intermediates. The rate constants of the individual processes have been determined by UV and 1H NMR spectroscopic techniques.