Nitromethane → 1-Nitrononadecan-2-ol

Participants

Reaction Steps

To a solution of octadecanal (9a) (2.22 g, 8.28 mmol) and nitromethane (1.52 g, 24.90 mmol) in anhyd Et2O (10 mL), Amberlyst A-21 (1.2 g) was added at r.t. The mixture was stirred and heated at reflux for 48 h. After removal of the Amberlyst A-21 by filtration, the filtrate was concentrated under reduced pressure. Flash column chromatography of the residue (EtOAc/petroleum spirit, 5/95) gave 1-nitrononadecan-2-ol (10a) (2.41 g, 89%) as a white solid; mp 55-56° C.

Provenance & Evidence