Hydrochloric Acid → 6-(4-Hydroxy-phenyl)-1-methoxy-naphthalen-2-ol

Participants

Reaction Steps

A mixture of 1-bromo-6-(4-hydroxyphenyl)-2-naphthol (0.41 g, 1.30 mmoles), CuBr (0.19 g, 0.13 mmoles), sodium methoxide (3 ml of 4.4 N in methanol), and DMF (6 ml) was heated to reflux for 3 hours. The reaction mixture was cooled to room temperature, poured into HCl (50 ml of 1N aqueous solution), and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with sodium bicarbonate solution, dried over sodium sulfate, filtered, stripped of solvent, and purified by silica column chromatgraphy (40% ethyl acetate-hexanes) to yield 0.31 g (89%) of the title compound as a white solid: mp 204–206° C.; 1H NMR (DMSO-d6): δ 6.88 (2H, d, J=8.47 Hz), 7.19 (1H, d, J=8.81 Hz), 7.57–7.60 (3H, m), 7.71 (1H, dd, J=1.41 J=8.78 Hz), 7.94–7.98 (2H, m), 9.54 (2H, s); MS m/z (M−H)−=265;

Provenance & Evidence