Hydrochloric Acid → Triphenylphosphine

Participants

Reaction Steps

Triphenylphosphine oxide (1.40 g, 5.0 mmol), granular aluminum (spherical, φ=3 mm, 2.13 g, 78.9 mmol) and acetonitrile (5 mL) were weighted out into a reactor, then oxalyl chloride (0.46 mL, 5.10 mmol) was added thereto under room temperature, and the mixture was stirred for 10 minutes. Then, lead bromide (17 mg, 0.05 mmol) was added to this reaction solution, and the mixture was stirred for 1 hour under room temperature to cause a reaction. The reaction solution was taken out with a syringe and poured into an iced 5% hydrochloric acid aqueous solution, and further, the granular aluminum was washed with ethyl acetate, and a wash liquid was also poured into the iced 5% hydrochloric acid aqueous solution as well. 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 (1.26 g, 4.82 mmol, yield: 96%) and triphenylphosphine oxide (28 mg, 0.10 mmol, collection rate: 2%) (first reaction).

Provenance & Evidence