2-Dimethylaminomethyl-4-chloro-1-naphthol → 2-Methyl-1-naphthol

Participants

Reaction Steps

A mixture of 14.18 g (60 m mole) 4-chloro-2-(dimethylaminomethyl)-1-naphthol (13) and 1.43 g 10% Pd-C in 240 ml ethanol was hydrogenated at 50 psi hydrogen atmosphere for 17 hours at room temperature then filtered over a layer of Celite. The filtrate was concentrated under reduced pressure. The residue was partitioned between water and ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and evaporated, whereby 8.99 g (representing a yield of 95%) 2-methyl-1-naphthol (1) were obtained: 1H NMR (300 MHz, DMSO-d6) δ2.32 (s, 3H), 7.21-7.40 (m, 4H), 7.75 (d, 1H, J=8 Hz), 8.15 (d, 1H, J=8 Hz), 9.01 (s, 1H, exch. with D2O); m/z 158 (M+).

Provenance & Evidence