Acetyl chloride → 4-Pyridinylacetone

Participants

Reaction Conditions

Reaction Steps

To 10 g of 4-methylpyridine and 32.75 g acetic anhydride, maintained at room temperature, was added 1 ml of acetyl chloride, dropwise over 5-10 min. The solution was then warmed to 50° C. for 6-16 hours. The black reaction mixture was then cooled to 0° C. and 100 mls of ethanol, was added dropwise. The reaction mixture was stirred for 1 hour after the addition, then refluxed for 4-12 hours. The alcohol was removed under reduced pressure and the residue taken up in 100-150 ml methylene chloride. The methylene chloride was washed 2 times with saturated 50 ml portions of sodium carbonate solution then dried over sodium sulfate and evaporated under reduced pressure. Toluene was added to the residue and the excess 4-methylpyridine removed by azeotropic distillation under reduced pressure. Yield: 4.3 gm of 4-pyridinyl-2-propanone.

Provenance & Evidence