Sodium Hydroxide → HCID 59544179, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Methyl 6-(1-methylcyclopropyl)-2-naphthoate (crude 0.91 g, 2.5 mmol) and 2M sodium hydroxide solution (3.8 ml) in methanol (7.6 ml) was heated at 60° C. for 2 hours. After cooling to room temperature, the mixture was washed with diethyl ether (100 ml). The aqueous layer was acidified to pH<3 with 2M hydrochloric acid solution and the mixture was extracted with dichloromethane-methanol (10:1, 150 ml×3 times). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give 0.444 g (78% yield for 2 steps) of the title compound as white solid. 1H NMR (300 MHz, DMSO-d6) ppm 0.77-0.92 (2H, m), 0.95-1.11 (2H, m), 1.49 (3H, s), 7.42 (1H, d, J=8.8 Hz), 7.84 (1H, s), 7.90-7.97 (2H, m), 8.01 (1H, d, J=8.8 Hz), 8.54 (1H, s). MS (ESI): m/z 225 (M−H)−.

Provenance & Evidence