Hydrogen Peroxide → 2,3,5-Trimethyl-1-oxidopyridin-1-ium

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Reaction Steps

420 ml of 30% hydrogen peroxide were added dropwise at room temperature to 246.4 g of 2,3,5-collidine and 2400 ml of glacial acetic acid. The solution was stirred at 80° overnight. The reaction mixture was then cooled to 40°, a further 420 ml of 30% hydrogen peroxide were added thereto and the mixture was heated to 80° for a further 24 hours. After evaporation in vacuo the residue was dissolved in 300 ml of water, whereupon the solution was made basic with concentrated sodium hydroxide solution while cooling, saturated with sodium chloride and extracted three times with 1 l of methylene chloride. The organic phases were dried over sodium sulfate and evaporated in vacuo. The residue was crystallized from ether/petroleum ether; there was obtained 2,3,5-trimethyl-pyridine 1-oxide of melting point 42°-44°.

Provenance & Evidence