Hydrochloric Acid → Triphenylphosphine

Participants

Reaction Steps

Triphenylphosphine oxide (1.405 g, 5.0 mmol) and acetonitrile (5 mL) were weighted out into a reactor, then oxalyl chloride (0.43 mL, 5.05 mmol) was added thereto under room temperature, and the mixture was stirred for 10 minutes. Then, previously shredded aluminum foil (135 mg, 5.0 mmol) and lead bromide (18 mg, 0.05 mmol) were added to this reaction solution, and subsequently the mixture was stirred for 1 hour under room temperature to cause a reaction. The reaction solution was poured into an iced 5% hydrochloric acid aqueous solution from the reactor, to terminate the reaction, and thereafter the organic layer was separated, and the water layer was extracted with ethyl acetate for 3 times. The organic layers were combined into one, washed with saturated saline, dried on sodium sulfate and concentrated under reduced pressure. The residue was purified with a silica gel column chromatography to give triphenylphosphine (1.189 g, 4.5 mmol, yield: 90%) and triphenylphosphine oxide (128 mg, 0.45 mmol, collection rate: 9%).

Provenance & Evidence