Acetonitrile → 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)prop-1-yl acetate

Participants

Reaction Steps

0.5 G. of 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propan-1-ol is dissolved in 15 ml. of acetonitrile and 2 ml. of acetyl chloride and 1.3 ml. of triethylamine are added to the solution. After 1 hour, the mixture is poured into water and extracted with ethyl acetate. The extract is dried and evaporated, then dissolved in ether and passed through a silica gel column, and the eluate evaporated to afford 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)prop-1-yl acetate [an oil, nmr spectrum in deuterochloroform relative to tetramethylsilane, 1.33 (doublet, CH3), 1.98 (singlet, acetoxy), 4.23 (doublet, CH2) and 7.02 ppm (singlet, 10H, 11H); mass spectrum: 306 (M+), 246, 234].

Provenance & Evidence