Acetyl migration during hydrogenation of p-nitrophenyl acetate

In connection with another problem, we wished to make p-aminophenyl acetate (II). Hydrogenation of p-nitrophenyl acetate (I), however, gives not p-aminophenyl acetate, but instead p-hydroxyacetanilide (III) and in high yield. The synthesis of III instead of p-aminophenyl acetate (II) could only have occurred through a new atypical para rearrangement of atoms heretofore unknown. This thesis presents a satisfactory chemical explanation of this novel rearrangement.