Hydrochloric Acid → 4,4,4-Trifluoro-2-methyl-1-(4-methylphenyl)butan-1-one

HRID 877197Notes

Reaction equation

HRID 877197 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([CH3:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[F:12][C:13]([F:21])([F:20])[CH2:14][CH:15]([CH3:19])[C:16](Cl)=[O:17].Cl>ClCCCl>[F:12][C:13]([F:21])([F:20])[CH2:14][CH:15]([CH3:19])[C:16]([C:8]1[CH:9]=[CH:10][C:5]([CH3:11])=[CH:6][CH:7]=1)=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 6451240Aluminum(III) ChlorideHCID 15104473HCID 15104473, compound

Product 1

HCID 581365984,4,4-Trifluoro-2-methyl-1-(4-methylphenyl)butan-1-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., 16.44 g (123.3 mmol) of aluminum chloride were added a little at a time to 12.6 ml (118.6 mmol) of toluene and 20.9 g (119.7 mmol) of 4,4,4-trifluoro-2-methylbutanoyl chloride in 300 ml of 1,2-dichloroethane, and the mixture was stirred at 0° C. for one hour. The reaction mixture was then slowly warmed to room temperature and stirred at this temperature for three hours. The reaction mixture was then slowly added to 300 ml of ice-cooled 18.5% strength hydrochloric acid, and the organic phase was then removed. The aqueous phase was extracted three more times with dichloromethane. The combined organic phases were dried over sodium sulfate and filtered, and the solvent was removed under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 4:1). This gave 19.96 g (18.7 mmol, 73% of theory) of the title compound.

Workup

  1. temperatureThe reaction mixture was then slowly warmed to room temperature
  2. stirringstirred at this temperature for three hours
  3. customthe organic phase was then removed
  4. extractionThe aqueous phase was extracted three more times with dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customThe crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-8691fa4028444c4fb365b9b54b027620
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

Loading…