Hydrochloric Acid → 1-Naphthol

Participants

Reaction Steps

To a slurry of 2.88 g (15 mmol) of 7-nitro-1-tetralone in 60 mL absolute ethanol was added 0.58 g (15 mmol) of sodium borohydride. The reaction mixture was then stirred at room temperature for 2 hours. The resulting mixture was then rotaevaporated to dryness and the residue obtained was suspended in 100 mL of water. 3 N hydrochloric acid was added dropwise until the reaction mixture had pH 7. The suspension obtained was then extracted with five 50 mL portions of ethyl ether and the combined ether layer was washed once with 100 mL water. The ether layer was dried over anhydrous sodium sulfate, filtered and rotaevaporated to give an off-white residue which was recrystallized from a 1:1 mixture of absolute ethanol and water to yield 2.68 g (92%) of the napthalenol; mp 112-113° C.; IR (KBr): 3300; 1H NMR: δ1.73-2.26 (4H, m), 2.29 (1H, s), 2.78-2.91 (2H, m), 4.83(1H, m), 7.24 (1H, d, J=8.1), 8.00-8.04 (1H, dd, J=8.1, 2.4), 8.35(1H, d, J=2.4),; 13C NMR: δ19.2, 29.9, 32.5, 68.3, 122.7, 124.1, 130.3, 140.9, 145.4.

Provenance & Evidence