Benzophenone → alpha,alpha-Diphenyl-4-pyridinemethanol

Participants

Reaction Steps

To a 500 mL RB flask were charged 4-cyanopyridine (10.4 g, 0.1 mole) and benzophenone (18.2 g, 0.1 mole). To this, xylene (250 mL) and sodium metal (5.0 g, 0.22 mole) cut into small pieces were added. The flask was heated slowly and refluxed under an inert atmosphere (e.g. nitrogen) with magnetic stirring for 3 hours. The color of the reaction mixture changed from clear to dark blue to dark brown during this time. The reaction mixture was cooled to room temperature and water was carefully added (150 mL). The solid product was filtered and washed with water and acetone. 4-Pyridyl diphenyl carbinol (18.3 g, 70% yield) was thus recovered with m.p. 238°-240° C.

Provenance & Evidence