Abstract
On treating 4-biphenylyl-4'-methyl benzoate (1) with anhydrous aluminum chloride (AlCl3) in o-dichlorobenzene at reflux temperature, 4-hydroxy-4'-methyl-3-biphenylyl phenyl ketone (3) was obtained as a rearrangement product with 4'-methyl-4-biphenylol (5). Then a rearrangement product 4-hydroxy-4'-methyl-3-biphenylyl methyl ketone (4) was obtained with 5 from 4-biphenylyl-4'-methyl acetate (2) under the same reaction conditions. The 4-biphenylyl ester 2 proceeded firster than other ester 1 in o-dichlorobenzene and toluene. A methyl group on 4'-position of 1 and 2 appeared to lose the reaction rate compared to 4-biphenylyl benzoate and 4-biphenylyl acetate. The Fries rearrangement of 1 may possibly proceed via an intramolecular pathway that involved some intermolecularity. Compoud 2 apparently proceeded via intramolecular rearrangement.
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