Ethanol → Ethyl 6-hydroxynaphthalene-1-carboxylate

Participants

Reaction Steps

Thionyl chloride (2.3 mL, 31.9 mmol) was slowly added to a solution of 6-hydroxy-1-naphthoic acid (3 g, 15.9 mmol) in ethanol (140 mL) and stirred under N2. After addition, the reaction mixture was heated at reflux under nitrogen for 6 days. The reaction mixture was cooled to room temperature and concentrated to give the crude product as an oil. The oil was carefully partitioned between 5% NaHCO3 and EtOAc. The organic phase was separated and washed with brine, dried over MgSO4, filtered and the filtrate was concentrated to give 3 g (87%) of the product as a red amorphous solid. 1H NMR (400 MHz, DMSO-d6): δ 9.92 (s, 1 H), 8.57 (m, 1 H), 7.92 (d, J=8 Hz, 1 H), 7.85 (d, J=7 Hz, 1 H), 7.45 (t, J=8, 1 H), 7.20-7.18 (m, 2 H), 4.38-4.33 (m, 2 H), 1.34 (t, J=7 Hz, 3 H).

Provenance & Evidence