Pyridine → Saligenin salicylate

Participants

Reaction Steps

Thionyl chloride (1 mol) in dichloromethane (400 ml) was added drop wise and with constant stirring to a dispersion of sodium salicylate (1 mol) in dichloromethane (800 ml). The mixture was stirred for a further hour, then left to cool to room temperature, care being taken to avoid absorption of atmospheric moisture. This solution was then added drop wise and with vigorous stirring to a solution of Product No. 1.1 (1 mol) and pyridine (2 mol) in dichloromethane (1200 ml). After addition was completed, the mixture was heated to 40° C., held at this temperature for 10 minutes and then allowed to cool. The reaction mixture was then washed several times with water and dilute acid until no traces of pyridine remained. The organic phase was then dried over anhydrous sodium sulphate, filtered and stripped of solvent to obtain saligenin salicylate in 60% yield.

Provenance & Evidence