Acetic Anhydride → 1-[(4R,4aR,7S,7aR,12bS)-7,9-dihydroxy-3-methyl-1,2,4,4a,7,7a,10,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl]ethanone

Participants

Reaction Steps

To a suspension of morphine (0.5 g, 1.75 mmol) in saturated NaHCO3 solution (25 mL), acetic anhydride (0.5 mL, 5.25 mmol) was added dropwise and allowed to stir for 3 hours. Progress of the reaction was monitored by TLC and after the completion; reaction mixture was extracted 6 times with dichloromethane. Dichloromethane layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to get solid 3-acetylmorphine. 0.34 g (59% yield). GC-MS, 1H and 13C NMR confirmed the structure.

Provenance & Evidence