Ethanol → Ethyl 4-(4-aminophenyl)butanoate

Participants

Reaction Steps

A solution of 10.0 g. of 4-(4-nitrophenyl)butyric acid in 150 ml. of ethanol containing 50 mg. of a 10% palladium on carbon catalyst is hydrogenated until the uptake of hydrogen ceases. After the system is purged with nitrogen and the solution is filtered through a celite pad, 3 ml. of boron trifluoride etherate is added and the solution is heated to reflux for 10 hours. Upon cooling and evaporation of the ethanol, a colorless residue is obtained. This product is recrystallized from ethanol-hexane and affords ethyl 4-(4-aminophenyl)butyrate.

Provenance & Evidence