Benzophenone → alpha,alpha-Diphenyl-4-pyridinemethanol

Participants

Reaction Steps

Sodium (16.6 grams, 0.72 mole) metal and xylene (150 ml) were charged into a 1 liter round bottom three-neck flask equipped with a mechanical stirrer, reflux condenser and two dropping funnels. The mixture was brought to reflux and the addition of benzophenone (54.6 grams, 0.3 mole) was begun. When about 1/4 to 1/3 of the benzophenone had added during 15-30 minutes, the addition of a solution of 4-cyanopyridine (38.2 grams, 0.37 mole) in xylene (200 mL) was begun at a rate so that about 1/2 of the cyanopyridine solution had been added when the addition of benzophenone was complete. The remaining cyanopyridine solution was added during another 30 minutes. Upon work-up with water (300 mL), 4-pyridyl diphenyl carbinol was obtained in about 95% yield.

Provenance & Evidence