2,5-Dimethylpyridine → 2,5-Dimethylpyridin-1-ium-1-olate

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Reaction Steps

2,5-Lutidine (1419 g) was dissolved in chloroform (13.5 L) and cooled to below 10° C. m-Chloroperoxybenzoic acid (70%, 3354.21 g) was added portion-wise to maintain the temperature at below 10° C., and then the reaction was warmed to room temperature and stirred overnight. Once no starting material was seen by tlc analysis, the mixture was cooled to 10° C. and quenched with aqueous 20% sodium hydroxide (2.5 L to 3 L) dropwise while maintaining a temperature below 20° C., which resulted in the formation of a very thick suspension. The mixture was stirred for 30 minutes and then allowed to separate. Water (5 L) was added, the organic layer was separated, and the aqueous layer was extracted twice with chloroform (4 L). The combined organic layers were washed with aqueous 1% sodium hydroxide, followed by aqueous 1N hydrochloric acid, and then concentrated under vacuum to give the desired product (1365 g).

Provenance & Evidence