Toluene → 4-(2,2-Diphenylethoxy)-pyridine-1-oxide

Participants

Reaction Steps

2,2-diphenylethanol (4 g, 0.02 m) was added portionwise to a suspension of sodium hydride (0.48 g, 0.02 m) in dry dimethylformamide (200 ml) under nitrogen. After the reaction had ceased, the mixture was added dropwise to a solution of 4-nitropyridine-1-oxide (2.8 g, 0.02 m) in dry dimethylformamide (100 ml) at 35°-40° C. The mixture was maintained at this temperature for 12 hours and then filtered. The solvent was removed under reduced pressure, leaving a residue that was heated with successive portions of toluene. The toluene solution was evaporated to an oil which was crystallised from a mixture of toluene and 60-80 petrol (1:1). This gave 4-(2,2-diphenylethoxy)pyridine-1-oxide (2.2 g) as orange crystals, m.pt. 134°-138° C.

Provenance & Evidence