2-Methoxyethanol → Ethanol

Participants

Reaction Steps

3.22 g (140 mmol) of metallic sodium was added to 70 ml of ethylene glycol monomethyl ether under ice-cooling and the mixture was stirred until no more hydrogen gas was produced. To the solution was dropwise added 25.0 g (123 mmol) of 2-chloro-3,5-dinitropyridine in 30 ml of ethylene glycol under ice-cooling over 5 minutes. After stirring for 30 minutes, the mixture was charged into 500 ml of saturated aqueous solution of ammonium chloride, followed by extraction with 400 ml of chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. Solvent was evaporated under reduced pressure to obtain yellow crystals. 24.5 g (101 mmol) of light yellow prismal crystals of the title compound was obtained by recrystallization from ethanol (yield: 82%).

Provenance & Evidence