Hinsberg and Udranszky (1) converted 2-aminophenol into the 0- ·benzoyl-N-benzoyl derivative by means of the Schotten-Baumann (2) reaction. Raiford and Inman (3) prepared a number of N-carboaryloxy derivatives of 2-aminophenol by following the method of Groenvik (4) who used ethyl chlorocarbonate as the only reagent. When these compounds were mixed with caustic alkali solution for the purpose of acylating them (2) they were converted into the corresponding benzoxazolones while the required phenols were eliminated. It was further shown that warming 2-N-carboaryloxyaminophenol with pyridine and with acetic anhydride, respectively, caused ring closure, and that in the latter instance there was formed Nacetylbenzoxazolone, previously prepared in a different way by Kalckhoff (5). This tendency toward ring formation is so great that when 2-benzoylaminophenol, in caustic alkali or pyridine solution, is treated with phenyl chlorocarbonate phenol is liberated and N-benzoylbenzoxazolone is obtained in yields as high as 85%. No diacyl derivatives of 2-aminophenol were obtained by this method.
Proceedings of the Iowa Academy of Science
©1944 Iowa Academy of Science, Inc.
Raiford, L. Chas and Dudley, J. R.
"Phenyl Chlorocarbonate and Substitution Products as Acylating Agents,"
Proceedings of the Iowa Academy of Science, 51(1), 313-317.
Available at: https://scholarworks.uni.edu/pias/vol51/iss1/30