Ethylene Glycol → 2-Pyridinyl-1,3-dioxolane

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Reaction Steps

A mixture of 2-pyridinecarboxaldehyde (300 g), 300 mL of ethylene glycol, 3 L of toluene and 100 g of p-toluenesulfonic acid in a 5 L 3 neck-flask equipped with a Dean-Stark head was refluxed for 4 h, separating the water formed. The mixture was concentrated in vacuo to 1/2 of its volume, and poured into a 5 L flask containing a cold (5° C.) sodium bicarbonate solution. The aqueous layer was extracted with methylene chloride (3×500 mL), the combined organic layer was dried over sodium sulfate, and concentrated in vacuo to yield a dark oil. The oil was distilled (1 mm/100°-110° C.) to afford 349.1 g (82.4%) of 2-(1,3-dioxolan-2-yl)pyridine.

Provenance & Evidence