The reduction of 1-naphthol (1) in dilute aqueous KOH using Ni-Al alloy as a reducing agent reported in the literature gave 5,6,7,8-tetrahydro-1-naphthol (2) in a high yield. The reinvestigation of this reaction under the same experimental conditions disclosed that the major products were 3,4-dihydro-2H- naphthalen-1-one (3) and 1,2,3,4-tetrahydro-1-naphthol (4) besides the formation of 2 as the minor product. The product distribution was examined and the possible mechanism was proposed. Accordingly, the reduction of 1-naphthol using Ni-Al alloy under alkaline conditions has provided a new synthetic pathway for the preparation of 3 and 4.

Key words: 3,4-dihydro-2H-naphthalen-1-one, 1-naphthol, 1,2,3,4-tetrahydro-1-naphthol, reduc-tion, Ni-Al alloy