Pyridine → N-(6-Acetoxyhexyl)-N-methylaniline

Participants

Reaction Steps

A mixture of 210 g (1.01 mol) of N-(6-hydroxyhexyl)-N-methylaniline, 112 g (1.10 mol) of acetic anhydride, and 86 g (1.1 mol) of pyridine was heated at reflux with stirring for 2 hours. After cooling, the solution was poured onto 500 g of ice and extracted with ethyl acetate (4×300 mL). The combined extracts were dried (MgSO4) and the solvent was removed at reduced pressure. The residue was distilled in vacuo, collecting the fraction boiling at 130° C. (0.01 mm). Yield: 231 g (93%) of a colorless oil.

Provenance & Evidence