Hydrochloric Acid → [4-(3-Pyridylmethyloxy)phenyl]propan-2-one

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Reaction Steps

A solution of (4-hydroxyphenyl)propan-2-one ethylene ketal (5 g) in ethanol (20 ml) was added to a stirred solution of sodium ethoxide in ethanol (1.26 g sodium in 50 ml). A suspension of 3-picolyl chloride hydrochloride (4.5 g) in ethanol (40 ml) was added, the mixture boiled for 41/2 hr, cooled and filtered. After evaporation of the solvent the residue was chromatographed on alumina. Elution with 10% methanol in dichloromethane gave a dark oil which was dissolved in methanol (50 ml) and boiled with 2M hydrochloric acid (40 ml) for 3 hours. Neutralisation with 2M sodium hydroxide solution followed by extraction into dichloromethane yielded an oil which was purified by bulb to bulb distillation at 70° C./0.4 mm to give [4-(3-pyridylmethyloxy)phenyl]propan-2-one.

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