Hydrochloric Acid → 1-(2-Chloro-4-methylphenyl)ethanone

Temperature

105 °C

A mixture of 2-chloro-4methylbenzonitrile (2.00 g, 13.19 mmol) in toluene (25 ml), was prepared at room temperature and 3M bromo methyl magnesium (13.2 ml, 39.68 mmol) in diethylether, 3M was added dropwise and the mixture then heated to reflux (100-110° C.) for 16 h. The mixture was then cooled to 0° C. and then adjusted to pH 2 with 2M aqueous HCl. The mixture was then heated to reflux as above for 2 h. The mixture was then basified with 2M NaOH to pH 11, extracted with EtOAc (100 ml), the organic phase dried over MgSO4 and then concentrated under reduced pressure. The crude product was then purified by column chromatography (0-10% EtOAc/Hexanes) to afford 1-(2-chloro-4-methylphenyl)ethanone as a pale yellow oil (1.60 g, 9.50 mmol, 72%).

1. customwas prepared at room temperature
2. temperaturethe mixture then heated
3. temperatureThe mixture was then cooled to 0° C.
4. temperatureThe mixture was then heated
5. temperatureto reflux as above for 2 h
6. extractionextracted with EtOAc (100 ml)
7. dry with materialthe organic phase dried over MgSO4
8. concentrationconcentrated under reduced pressure
9. customThe crude product was then purified by column chromatography (0-10% EtOAc/Hexanes)

ORD record

ord-b218061fddcf45bfa57c9bfa655260fd

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115088B2