Water → 2-Ethyl-1-(4-methoxyphenyl)butan-1-one

Participants

Reaction Steps

Dysprosium (III) trifluoromethanesulfonate (3.66 g as a wet solid), anisole (1.08 g) and 2-ethylbutanoic acid (1.16 g) were refluxed together in 125 mL toluene with azeotropic removal of the lower water layer (Dean-Stark apparatus). After 48 hours, the mixture was cooled and extracted with 3×25 mL water, then by 2×25 mL saturated sodium bicarbonate solution. The organic layer was dried using anhydrous sodium sulfate, filtered, then concentrated down in vacuo to give para-methoxy-2-ethylbutyrophenone (0.90 g, 44% yield) as an amber-colored oil, which was practically pure by 1H NMR analysis. Removal of water from the three water extracts recovered 3.54 g as a damp, off-white solid.

Provenance & Evidence