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

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).

1. temperaturewas refluxed for 16 h
2. customthe solvent was removed
3. additionWater (100 mL) was added to the residue
4. extractionthe mixture was extracted with Et2O (3×50 mL)
5. washThe combined organic layers were washed with brine (50 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated to dryness
8. distillationThe resulting yellow oil was distilled under reduced pressure (0.1 Torr)
9. distillationthe fraction that distilled at 110° C.

ORD record

ord-6a9655f6462949939d2c42d9f080f19e

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09095589B2