p-Toluenesulfonic acid → 1-Benzhydryl-3-(2,4,4'-trichlorobenzhydryloxy)azetidine

Participants

Reaction Steps

A solution of 2,4,4′-trichlorobenzhydrol (2) (174 mmol), p-toluenesulfonic acid (174 mmol) and 1-benzhydryl-3-azetidinol (1) (87 mmol) in toluene (700 mL) was heated at reflux under Dean-Stark conditions for 30 minutes. The solution was cooled, washed with sodium hydrogen carbonate (saturated aqueous solution, 700 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography [SiO2; (10% ethyl acetate:isohexane)] to furnish the product as a yellow oil (22.0 g, 50%).

Provenance & Evidence