Acetic Anhydride → N-(2-Acetoxyethyl)-N-methylaniline

Participants

Reaction Steps

A solution of 74.0 g (0.489 mol) of N-(2-hydroxyethyl)-N-methylaniline in 100 mL of pyridine was treated dropwise with 55 g (0.54 mol) of acetic anhydride. The resulting mixture was heated at reflux for 10 hr, then cooled and poured onto 500 g of ice. The mixture was extracted three times with dichloromethane (3×100 mL), the combined extracts were dried using magnesium sulfate (MgSO4) and the solvent was evaporated. The residue was distilled at reduced pressure, producing 84.2 g of a slightly yellow oil, b.p. 107°-116° C. (0.4 mm).

Provenance & Evidence