Pyridine → 1-(2-Chlorophenyl)propane-1,2-dione

Participants

Reaction Steps

To a solution of 2-chlorophenylacetone (10.800 g, 64.049 mmol) in 279 mL of CH2Cl2, pyridinium chlorochromate (41.418 g, 192.15 mmol), and pyridine (16 mL) in three portions were added over 2.5 hours and the mixture was refluxed under vigorous stirring. After 22 h, the mixture was removed from heat. The mixture was concentrated in vacuo to give a dark red syrup. The crude mixture was purified by column chromatography on a 120 g of Redi-Sep™ column using 0-10% gradient of EtOAc in hexane over 28 min as eluent to give 1-(2-chlorophenyl)propane-1,2-dione as yellow liquid: 1H NMR (400 MHz, chloroform-d) δ ppm 7.66 (1 H, dd, J=7.6, 1.8 Hz), 7.49-7.54 (1 H, m), 7.38-7.45 (2 H, m), 2.58 (3 H, s); LC-MS: m/z 182.9 [M+H]+.

Provenance & Evidence