Hydrochloric Acid → 2,2-Dimethyl-1-(4-methylphenyl)-1-propanone

To a suspension (200 ml) of magnesium (7.14 g, 294 mmol) in ether in a three necked flask was added dropwise a solution of p-bromotoluene (34 ml, 276 mmol) in ether (100 ml), and the mixture was heated under reflux for 1.5 hrs. Thereafter, to the mixture was added a solution of trimethylacetonitrile (25 ml, 226 mmol) in ether (100 ml), and the mixture was stirred for 2 hrs. The mixture was then ice-cooled. To the mixture was added dropwise 6N hydrochloric acid, and the mixture was stirred at room temperature for 30 min. The mixture was diluted with ether, and washed with water and saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0, 10:1) to give 2,2-dimethyl-1-(4-methylphenyl)-1-propanone (10.94 g, 27%) as a colorless transparent oil.

1. temperaturethe mixture was heated
2. temperatureunder reflux for 1.5 hrs
3. temperatureice-cooled
4. stirringthe mixture was stirred at room temperature for 30 min
5. washwashed with water and saturated brine
6. dry with materialThe mixture was dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0, 10:1)

ORD record

ord-261f619fdb4c4009846c407d71492bb1

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06982348B2