4'-Hydroxyacetophenone → Benzyl [2-(4-acetylphenoxy)ethyl]carbamate

Participants

Reaction Steps

A mixture of 35 g of 2-(N-benzyloxycarbonylamino)ethyl p-toluenesulfonate, 13 g of 4'-hydroxyacetophenone and 55 g of anhydrous potassium carbonate in 450 ml of dry acetone was refluxed with stirring for 24 hrs under argon atmosphere. After cooling, the insoluble material was removed by filtration and the filtrate was evaporated. The residue was diluted with ethyl acetate, washed with water, 1% NaOH and brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to give a solid, which was recrystallized from hexane-benzene to give 26.5 g of 4'-(2-(N-benzyloxycarbonylamino)ethoxy)-acetophenone as white needles.

Provenance & Evidence