Oxalyl chloride → 2-Benzoyl-6-methylpyridine

Participants

Reaction Steps

To 15 g of 6-methyl-2-pyridylcarboxylic acid (122 mmol) in 200 ml benzene is added dropwise 19.1 g (150 mmol) oxalyl chloride (dissolved in 30 ml benzene) with ice bath cooling. The solution is allowed to come to RT and is stirred 1 hour, after which it is stripped, 100 ml of benzene is added, and it is stripped again. The residue is taken up in 200 ml benzene and 41 g of aluminumtrichloride (310 mmol) is added in portions over a 3 hour period with ice bath cooling. The solution is heated to 25° for 1 hour, then heated to reflux for 2 hours, and finally cooled and stirred overnight. The mixture is poured onto ice/conc. HCl, then washed with ether. Fifty Percent (50%) sodium hydroxide is added until the precipitate is dissolved. The solution is extracted with CHCl3, washed with water, dried and stripped, leaving 6-benzoyl-2-methylpyridine.

Provenance & Evidence