Ethanol → 1-Naphthol

Participants

Reaction Conditions

Reaction Steps

Naphthylether 10 (19.8 g, 81 mmol) was dissolved in a dry DCM (400 mL) and the solution cooled to −70° C. A solution of BBr3 (1M in DCM, 160 mL, 160 mmol) was added dropwise while maintaining an internal temperature below −60° C. The mixture was aged at this temperature for an additional 30 min, then allowed to warm up to RT and aged for additional 2 h at rt. The mixture was then again cooled to −70° C., treated with absolute ethanol (20 mL), and the resulting mixture was aged at rt overnight. The solution was poured into a cold NaHCO3 solution (500 mL, saturated aq) and vigorously stirred. The organic layer was washed with dilute HCl solution (0.1N, 200 mL) and with water (200 mL), and the solvent removed. Column chromatography of the resulting residue using 20% ethyl acetate in hexanes yielded the naphthylester 12 (17.6 g, 76.4 mmol) in 94% yield.

Provenance & Evidence