Ammonia → Triphenylsulfonium toluenesulfonate

Participants

Reaction Steps

Diphenyliodonium dimethylphosphate (315 mg; 1 mmol) and p-toluenesulfonic acid (189 mg; 1.1 mmol) were dissolved in methylene chloride (10 ml), and the mixture was stirred, followed by addition of 1% aqueous ammonia (10 ml). After the alkalinity of the solution was confirmed, the solution was stirred vigorously. The thus-obtained mixture was allowed to stand, and the aqueous layer was separated. The aqueous layer was washed with water successively until the aqueous layer exhibited neutral pH. The methylene chloride solution was dried, and the solvent was removed through distillation. The residue was washed in ether by stirring, to thereby precipitate 214 mg of the target compound as white crystals (yield: 84%).

Provenance & Evidence