Water → 1-Benzhydryl-3-phenoxyazetidine

Participants

Reaction Conditions

Reaction Steps

To a suspension of 8.6 g (0.22 mole) of sodium amide in 100 mL of dry toluene was added 18.8 g (0.2 mole) of phenol in 50 mL of dry toluene. The mixture was stirred at 60° C. for 2 hr. and the reaction temperature raised to 80° C. A solution of 63.4 g (0.2 mole) of 1-benzhydryl-3-methanesulfonyloxyazetidine (J. Org. Chem. 37, 3954 (1972)) in 200 ml of dry toluene was added dropwise. After stirring 2 hr at 80° C. the mixture was cooled and water added. The toluene was extracted with dilute NaOH solution, dried (Na2SO4) and concentrated. About one-third of the residue was removed. The rest of the residue was crystallized twice from water-isopropyl alcohol. Yield 9.3 g (15%); m.p. 83°-85° C.

Provenance & Evidence