2-Chloropyridine → Butyl 2-pyridyl ether

Participants

Reaction Conditions

Reaction Steps

Into a solution of 55 g (1,38 mole) of sodium hydroxide in 245 g of n-butanol heated to 100° C., were added dropwise over four hours 113.5 g (1 mole) of 2-chloropyridine and the mixture was stirred for about 15 hours at this temperature, then heated for 2 hours at reflux (ca. 112° C.). After cooling, precipitated sodium chloride was removed by filtering and the residue was washed with about 500 ml of n-butanol. The combined filtrates were distilled in vacuum and the first fraction to distill was a butanol-water azeotrope, then followed n-butanol and a 2-chloropyridine/n-butanol intermediate run. 2-butoxypyridine distilled last at 75° C. at 10 Torr as a colorless liquid to obtain 108 g (72%) of 2-butoxypyridine with a purity of >98%.

Provenance & Evidence