6-Methoxy-alpha-tetralone → 6-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Participants

Reaction Steps

Aqueous HBr (100 mL) was added to 6-methoxy-1-tetralone (10.0 g, 56.8 mmol), and the reaction mixture was refluxed for overnight. The reaction mixture was then brought to room temperature and extracted with ethyl acetate (2×100 mL). The organic layer was dried over sodium sulphate, filtered and removed under reduced pressure. The crude product was purified using flash chromatography using 40% ethyl acetate in hexanes to afford title compound (8.0 g, 86%) as solid. 1H NMR (400 MHz, CDCl3): δ 7.99 (d, J=8.0 Hz, 1H), 6.78 (d, J=8.4 Hz, 1H), 6.69 (s, 1H), 6.23 (bs, 1H), 2.9 (t, J=6.0 Hz, 2H), 2.62 (t, J=6.0 Hz, 2H), 2.11 (m, 2H); ESI-MS m/z=163 (M+H)+.

Provenance & Evidence