Hydrochloric Acid → 1-(4-Chloro-2-methylphenyl)ethan-1-one

Temperature

40 °C

Methylmagnesium bromide (6.29 g, 52.8 mmol) was added to a stirred solution of 4-chloro-2-methyl-benzonitrile (5.00 g, 33.0 mmol) in diethyl ether (44 mL). The mixture was heated to 40° C. After 72 h the mixture was cooled to room temperature and poured into a stirred mixture of anhydrous diethyl ether (120 mL), ice water (100 mL), and 10% aqueous HCl (100 mL). The aqueous layer was separated, stirred at reflux for 1 h, then was cooled to room temperature and was extracted into diethyl ether (4×50 mL). The organic layers were combined, washed with saturated NaHCO3 and brine, dried (Na2SO4) and concentrated in vacuo. 1-(4-Chloro-2-methylphenyl)ethanone was obtained as an oil. 1H NMR (CDCl3, 400 MHz) δ 2.52 (s, 3H), 2.56 (d, J=0.7 Hz, 3H), 7.24 (m, 2H), 7.65 (d, J=8.8 Hz, 1H).

1. temperatureAfter 72 h the mixture was cooled to room temperature
2. customThe aqueous layer was separated
3. temperatureat reflux for 1 h
4. temperaturewas cooled to room temperature
5. extractionwas extracted into diethyl ether (4×50 mL)
6. washwashed with saturated NaHCO3 and brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated in vacuo

ORD record

ord-c46552669f4a4056ab1369f51250ffc7

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07144899B2