Acetic Acid → 1-(5-Cyclohexyl-2-hydroxyphenyl)ethan-1-one

Participants

Reaction Steps

35.25 g of 4-cyclohexyl-phenol were added in small amounts at 5° to 10° C. to a solution of 46 g of boron trifluoride in 110 ml of concentrated acetic acid and the mixture was held at 50° C. for 15 minutes and then at 75° C. for 21 hours. The mixture was poured into ice and the aqueous phase was extracted 3 times with 200 ml of ether. The ether phase was treated with powdered sodium bicarbonate and was stirred for 16 hours and was then filtered. The filtrate was washed with water until the wash water was neutral, dried over magnesium sulfate and was evaporated to dryness under reduced pressure. The residue was pressure chromatographed over silica gel and was eluted with a 1-4 ether-petroleum ether (b.p.=60° to 80° C.) mixture to obtain 39.9 g of 1-(2-hydroxy-5-cyclohexylphenyl)-ethanone melting at <50° C.

Provenance & Evidence