Picolyl chloride hydrochloride → [4-(2-Pyridylmethyloxy)phenyl]propan-2-one

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Reaction Steps

A solution of (4-hydroxyphenyl)propan-2-one ethylene ketal (28 g) in ethanol (40 ml) was added to a stirred solution of sodium ethoxide in ethanol (7.1 g of sodium in 100 ml) and the resulting solution stirred at room temperature for 20 minutes. A suspension of 2-picolyl chloride hydrochloride (25 g) in ethanol (60 ml) was added and the resulting mixture was boiled under reflux for 5 hours, cooled and filtered. 2M Hydrochloric acid (100 ml) was added, the solution boiled for 5 h, cooled and neutralised with 2M sodium hydroxide solution. After dilution with water the solution was extracted with dichloromethane and the washed organic phase dried and evaporated to give a dark oil. Bulb to bulb distillation gave [4-(2-pyridylmethyloxy)phenyl]propan-2-one, b.pt. 96°-100° C./0.2 mm, which was used without further purification.

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