Hydrochloric Acid → 1-Allyl-4-hydroxy-1-methylnaphthalen-2(1h)-one

Participants

Reaction Steps

To a solution of Example 123C (2.69 g, 11.8 mmol) in methanol (75 ml) was added a solution of 1N aqueous sodium hydroxide (75 mL) and the resultant mixture heated to reflux for 16 hours. After cooling to room temperature a solution of 1N aqueous hydrochloride (80 mL) was added to make the mixture acidic which caused a precipitate to form. This solid was collected by filtration, washed with water (5×20 mL) and dried in a vacuum oven to provide the title compound as a light brown solid (1.97 g, 78%). 1H NMR (300 MHz, DMSO-d6): δ 1.44 (s, 3 H), 2.65 (dd, J=13.2, 7.0 Hz, 1 H), 2.80 (dd, J=13.6, 7.0 Hz, 1 H), 4.72 (m, 2 H), 5.08 m, 1 H), 5.66 (s, 1 H), 7.36 (dt, J=7.2, 1.3 Hz, 1 H), 7.56 m, 1 H), 7.65 (d, J=7.7 Hz, 1H), 7.89 (d, J=7.7 Hz, 1 H).

Provenance & Evidence