1-Butanol → HCID 68471813, compound

Participants

Reaction Conditions

Reaction Steps

A 22 Liter reaction flask is equipped with a heating mantle, overhead stirring apparatus, condenser, addition funnel, thermometer probe, and nitrogen inlet/outlet. The flask is purged thoroughly with nitrogen and maintained under nitrogen throughout the reaction. The flask is charged with 4-nitrobiphenyl (1700 g, 8.53 moles) and 1-butanol (3793 g, 51.2 moles). The resulting mixture is heated to reflux to form a clear solution. Tributylphosphine (3500 g, 17.3 moles) is charged to the addition funnel and added dropwise to the hot 4-nitrobiphenyl solution. The temperature is gradually increased as needed to maintain reflux. The reaction is monitored by gas chromatography analysis for completion. The reaction is cooled and water is added (500 mL). The reaction is concentrated to an oil, followed by the addition of petroleum ether (8.0 L). The resulting mixture is cooled to −40° C. and filtered to remove undesired tributylphosphine oxide. The filtrate is concentrated again and petroleum ether (8.0 L) is added. The mixture is cooled and filtered. The resulting filtrate is concentrated to an oil and purified by silica gel chromatography to give the title compound (908 g, 44%).

Provenance & Evidence