Benzyl Alcohol → benzyl N-ethenylcarbamate

Participants

Reaction Conditions

Reaction Steps

Into a 500 mL single neck flask were placed benzyl alcohol (76.5 mL, 792 mmol), hydroquinone (3.05 g, 27.7 mmol), pyridine (3 mL, 27.7 mmol) and the mixture was stirred at 100° C. while treated with the toluene solution of 1-aza-1-diazobuta-1,3-dien-2-one (200 mL) dropwise. The mixture was stirred at 110° C. for 30 minutes and at RT for 12 hours. The reaction mixture was concentrated and the resulting crude oil was distilled under reduced pressure (0.4 mm Hg) to provide the intermediate title compound, (phenylmethoxy)-N-vinylcarboxamide, (43.1 g, 45%) as a pure oil (came out at 110-115° C.) which solidified upon sitting at RT. Electron spray M.S. 178 (M*+H) Analysis for C10H11NO2:

Provenance & Evidence