Acetyl chloride → 1-(1-Hydroxy-4-methoxynaphthalen-2-yl)ethan-1-one

Participants

Reaction Steps

A solution of 4-methoxy-1-naphthol 11 (435 mg, 2.5 mmol) in toluene (5 mL) and nitromethane (0.75 mL) was treated with scandium triflate (61.52 mg, 0.125 mmol) and acetyl chloride (0.195 mL, 2.75 mmol) and irradiated in the microwave reactor (Personal Chemistry, Inc) at a temperature of 170° C. for 5 minutes. The cooled reaction was diluted with methylene chloride and filtered through a small pad of silica gel. The filtrate was evaporated to dryness and purified via flash chromatography, eluting the pure C-acylated product 12 with CH2Cl2/hexanes (1:1). Pooled fractions were evaporated to afford 12 as a greenish yellow solid (0.388 g, 72% yield). 1H NMR (300 MHz, CDCl3): δ 2.69 (s, 3H, COCH3), 3.99 (s, 3H, OCH3), 6.84 (s, 1H, Ar-3-H), 7.80 (m, 2H, Ar—H), 8.10 (d, 1H, Ar—H), 8.21 (d, 1H, Ar—H), 13.76 (s, 1H, OH).

Provenance & Evidence