Acetic Acid → 1-[4-Methoxy-3-(trifluoromethyl)phenyl]ethan-1-one

Participants

Reaction Steps

A solution 1-methoxy-2-(trifluoromethyl)benzene (3.52 g) was dissolved in glacial acetic acid (30 ml) and treated with boron trifluoride acetic acid complex (30 ml) and the resulting solution maintained at 55° for 48 hours. The solution was poured into dilute hydrochloric acid (100 ml) and ice (100 g) added and the mixture extracted with chloroform (2×200 ml). The combined organic extracts were washed with sodium bicarbonate solution (3×100 ml), then water (100 ml), dried and evaporated to dryness to give an oily black solid. This was chromatographed on silica (40 g) eluting with ether:light petroleum (bp.60°-80°) (1:4) to give a solid which was crystallised from light petroleum (bp.60°-80°) to give the title compound (0.3 g), m.p.56°-57°

Provenance & Evidence