N-Methylaniline → 6-[Methyl(phenyl)amino]hexan-1-OL

Participants

Reaction Steps

A mixture of 153 g (1.43 mol) freshly distilled N-methylaniline, 200 g (1.46 mol) 6-chlorohexanol, 200 g (1.45 mol) potassium carbonate, 6 g potassium iodide, and 750 mL n-butanol was heated at reflux under nitrogen with vigorous mechanical stirring for 4 days. The solution was cooled, filtered, and the solvent was removed at reduced pressure. The residue was distilled in vacuo to produce 210 g (71%) of a colorless oil, bp 153°-166° C. (0.10 mm).

Provenance & Evidence