1-Chloro-4-(chloromethyl)benzene → 4-(4-Chlorophenyl)butan-2-one

Participants

Reaction Steps

A mixture of 4-chlorobenzyl chloride (8.05 g, 55 mmol), acetylacetone (5.20 mL, 50 mmol), K2CO3 (6.90 g, 50 mmol), and anhydrous ethanol (50 mL) was refluxed for 16 h. The reaction mixture was cooled to room temperature and the solvent was removed. Water (100 mL) was added to the residue and the mixture was extracted with Et2O (3×50 mL). The combined organic layers were washed with brine (50 mL) and dried over Na2SO4 and concentrated to dryness. The resulting yellow oil was distilled under reduced pressure (0.1 Torr) and the fraction that distilled at 110° C. was collected as a clear, colorless oil (6.15 g, 67% yield).

Provenance & Evidence