Isobutylbenzene → 1-(4-(2-Methylpropyl)phenyl)-1-propanone

HRID 249146

Reaction equation

HRID 249146 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:11]([CH3:13])[CH3:12]>ClCCl>[CH2:10]([C:14]1[CH:19]=[CH:18][C:17]([C:1](=[O:4])[CH2:2][CH3:3])=[CH:16][CH:15]=1)[CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 10870IsobutylbenzeneHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1088341-(4-(2-Methylpropyl)phenyl)-1-propanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Propionyl chloride (13.0 ml) was added to a suspension of aluminum chloride (20.0 g) in dichloromethane (200 ml) at 0° C. After the mixture was stirred at 0° C. for 1 hour, isobutylbenzene (23.6 ml) was added to the mixture. The mixture was stirred at 0° C. for 2 hours and poured into ice water. The organic layer was washed with water, dried over magnesium sulfate and evaporated. The residual oil was distilled under reduced pressure to give 4'-isobutylpropiophenone as a colourless oil (24.4 g).

Workup

  1. stirringThe mixture was stirred at 0° C. for 2 hours
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. distillationThe residual oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-dd0074dde56f45898c7b4046bbf60793
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Linked notes

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