Resorcinol → 1-(2,4-dihydroxyphenyl)-3-methylbutan-1-one

Participants

Reaction Conditions

Reaction Steps

Add isovaleric acid (5.10 g, 50 mmol, 5.5 mL) in one portion to a mixture of resorcinol (5.00 g, 45.4 mmol) in boron trifluoride etherate (38.67 g, 272.5 mmol, 34.5 mL) at room temperature under Argon gas. Heat the reaction mixture at 90° C. for 1.5 hr. Cool the reaction to room temperature and pour it into a 20% aqueous sodium acetate solution and stir overnight. Extract the aqueous mixture with ethyl acetate (3×). Combine the organic layers, wash with saturated aqueous sodium bicarbonate solution and brine sequentially. Dry the organic phase over sodium sulfate, filter and concentrate under reduced pressure to provide the product as a brownish oil (9.80 g; 50.5 mmol, 111% yield). MS (m/z): 195 (M+1).

Provenance & Evidence