FRIES REARRANGEMENT OF PHENYL 1-NAPHTHYLA CETATES AND 2-NAPHTHYLACETATES

In the reaction of phenyl 1-naphtylacetate(1alpha) with anhydrous alum inum chloride(AlCl3), 2'-hydroxy-2-(1-naphtyl)acetophenone(2) and 4'-h ydroxy-2-(1-naphtyl)acetophenone(3) were obtained as the rearrangement products. Similarly, 2'-hydroxy-2-(2-naphtyl)acetophenone(4) and 4'-h ydroxy-2-(2-naphtyl)acetophenone(5) were given in the Fries rearrangem ent of phenyl 2-naphtylacetate(1beta). [GRAPHICS] Fries rearrangement of 1alpha and 1beta seems to proceed mainly via intramolecular pathway . Retro-Fries rearrangement and isomerization of rearrangement product s (2, 3, 4 and 5) also proceed intramolecularly. When nitrobenzene was used as a solvent in the Fries rearrangement of 1alpha and 1beta, the reaction proceeded smoothly with lower ortho-para ratio (2/3 and 4/5) in compared with the case of chlorobenzene used.