4'-Hydroxyacetophenone → 1-(4-Propoxyphenyl)ethan-1-one

Participants

Reaction Steps

To 272 g (2000 mmole) of 4'-hydroxyacetophenone dissolved in 800 ml of ethanol was added 249 g (2000 mmole) of 45% aqueous potassium hydroxide. After stirring for 5 minutes, 270 g (2200 mmole) of 1-bromopropane was added and the mixture was refluxed for 6 hours. After cooling, the precipitated potassium bromide was filtered off and washed with diethyl ether. The combined organic layers were concentrated in vacuo and then redissolved in 500 ml of diethyl ether. The resulting solution was washed with 1M aqueous sodium hydroxide solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo yielding 270 g of the expected product, an oil, bp 110° C. at 1 torr.

Provenance & Evidence