Hydrochloric Acid → 2-Hydroxy-1-naphthalen-1-yl-propan-1-one

Participants

Reaction Steps

A solution of acetic acid 1-naphthalen-1-yl-2-oxo-propyl ester and acetic acid 1-methyl-2-naphthalen-1-yl-2-oxo-ethyl ester (2:1 mixture) (16.7 g), ethanol (300 mL) and 1M hydrochloric acid (150 mL) was heated at reflux for 4 hours. After cooling to room temperature, the ethanol was removed under reduced pressure and the aqueous phase was extracted with dichloromethane (200 mL). The organic phase was washed with water (2×150 mL), brine (2×150 mL) dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to afford 1-hydroxy-1-naphthalen-1-yl-propan-2-one and 2-hydroxy-1-naphthalen-1-yl-propan-1-one (4:1 mixture) (12.0 g, 87%) as an orange oil, 1H NMR (DMSO-D6): 1.2 (3H, d, J=6.8 Hz), 2.0 (3H, s), 5.0 (1H, m), 5.35 (1H, d, J=6.5 Hz), 5.65 (1H, d, J=4.0 Hz), 6.15 (1H, d, J=4.0 Hz), 7.45-8.20 (10H, m).

Provenance & Evidence