5-Methoxytetralone → 5-Methoxynaphthalen-1-ol

Participants

Reaction Steps

In a 2000 ml flask a mixtuere of 5-methoxy-1-tetralone (30.0 g, 170.2 mmol) and 10% Pd/C (40 g) in 1000 ml p-cymenewas brought to reflux and monitored by LC-MS until no more starting material was present (approx. 24 h). The mixture was then cooled to room temperature and passed through a silica gel/celite plug and concentrated under vacuum to 26.6 g (90%) of an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ 3.90 (3H, s), 6.83 (1H, appd, J=7.5 Hz), 6.89 (1H, appd, J=7.7 Hz), 7.24 (1H, appt), 7.30 (1H, appt), 7.54 (1H, appd, J=8.5 Hz), 7.65 (1H, d, J=8.5 Hz), 9.98 (1H, s).

Provenance & Evidence