The Oxidation of Some Naphthols with Benzoyl Peroxide.

The reactions of four naphthols (1-naphthol (1), 2-naphthol (2), 4-isopropyl-1-naphthol (18), and 3-isopropyl-2-naphthol (19)) with benzoyl peroxide were examined under two reaction conditions (A and B). Each of the naphthols 1, 2, 18, and 19 was oxidized with 0.95 equivalent moles of benzoyl peroxide at room temperature for 24 h (condition A) to give mainly the corresponding ortho-benzoyloxylated product which was isolated in moderate yield as an equilibrium mixture, resulting from its trans -benzoylation. The naphthols 18 and 19 were also oxidized with 2.25 equivalent moles of benzoyl peroxide at room temperature for 48 h (condition B) to give mainly 2,2-bis(benzoyloxy)-4-isopropyl-1(2H)-naphthalenone and 2,2-bis(benzoyloxy)-3-isopropyl-1(2H)-naphthalenone in good yields. The oxidations of 1 and 2 under condition B produced the same product, 2,2-bis(benzoyloxy)-1(2H)-naphthalenone, in low yields.