Isobutylbenzene → 1-(4-(2-Methylpropyl)phenyl)-1-propanone
Reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH2:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:6]([CH3:8])[CH3:7].[C:15](Cl)(=[O:18])[CH2:16][CH3:17]>C(Cl)Cl>[CH2:5]([C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:18])[CH2:16][CH3:17])=[CH:11][CH:10]=1)[CH:6]([CH3:8])[CH3:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
To a mixture of 74.91 g of anhydrous aluminum trichloride and 300 ml of dry methylene chloride, maintained at about -10° C. in a salt-ice bath, is added a mixture of 67.1 g of isobutylbenzene and 46.77 g of propionyl chloride over a 90 minute period, while maintaining the temperature at between about -5° C. to 0° C. The reaction mixture then is stirred for an additional 30 minutes, quenched with a dilute hydrochloric acid solution and extracted with methylene chloride. The aqueous layer is separated and extracted twice more with methylene chloride and then the combined methylene chloride extracts are washed with water and saturated sodium bicarbonate. The organic extracts then are dried over magnesium sulfate, filtered and the methylene chloride is removed on a rotary evaporator to yield 1-(4-isobutylphenyl)propan-1-one.
Workup
- additionis added
- temperaturewhile maintaining the temperature at between about -5° C. to 0° C
- customquenched with a dilute hydrochloric acid solution
- extractionextracted with methylene chloride
- customThe aqueous layer is separated
- extractionextracted twice more with methylene chloride
- washthe combined methylene chloride extracts are washed with water and saturated sodium bicarbonate
- dry with materialThe organic extracts then are dried over magnesium sulfate
- filtrationfiltered
- customthe methylene chloride is removed on a rotary evaporator
Sources & evidence
- ORD record
- ord-3354e9fab1ce4e7ab244eec4b45be6eb
- Source dataset
- uspto-grants-1987_03
- Patent number
- US04654438
Reaction notes
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