Benzoyl chloride → 1-Phenyl-2-(4-pyridinyl)ethanone

Participants

Reaction Conditions

Reaction Steps

30.2 g of benzoyl chloride dissolved in 30 cc of dichloromethane was added dropwise over 1 hour to 10 g of 4-methylpyridine dissolved in 60 cc dichloromethane and maintained at 10° C. during the addition. The reaction was brought to room temperature and stirred 16 hours. The reaction was brought to reflux for 1 hour, then cooled and quenched into saturated sodium carbonate solution. The organic layer was separated, solvent removed under reduced pressure and alcohol added. The mixture was refluxed 16 hours, then the solvent removed under reduced pressure. The residue was taken up in dichloromethane and washed two times with 3N HCl. The organic layer was separated and the aqueous acid layer first neutralized, then saturated with sodium carbonate. Dichloromethane extraction of the product, solvent removal and azeotropic removal of excess unreacted 4-methylpyridine using toluene gave 4.85 g of desired product.

Provenance & Evidence