Toluene → 1-Propanone, 2-methyl-1-(4-methylphenyl)-
Reaction equation
[CH:1]([CH:4]1[C:12]2[C:7](=[CH:8][C:9]([CH3:13])=[CH:10][CH:11]=2)C(C)(C)C1C)([CH3:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)(=[O:25])C(C)C.C1(C)C=CC=CC=1>[N+](C)([O-])=O>[CH:1]([C:4]([C:12]1[CH:7]=[CH:8][C:9]([CH3:13])=[CH:10][CH:11]=1)=[O:25])([CH3:3])[CH3:2]Participants
Conditions
- Temperature
- 10 °C
Procedure
To prepare 1-isopropyl-2,3,3,5-tetramethylindane, the procedures of Traas et al., U.S. Pat. No. 4,352,748 are substantially followed. Specifically, a solution of aluminum chloride (75 g) in nitromethane (50 ml) is added to a mixture of isobutyroyl chloride (49 g), nitromethane (50 ml) and toluene (100 ml), and stirred for one hour at about 10° C. The reaction mixture is poured over ice and extracted with ether. The ether solution is washed to neutrality, dried and evaporated. The residue is distilled under diminished pressure to obtain p-tolyl isopropyl ketone. The ketone (11 g) is then dissolved in methanol (50 ml), added to a solution of NaBH4 (10 g) in a methanol/water mixture (100 ml; 1:1). The reaction mixture is stirred for one hour, and then poured into water and extracted with ether. The solution in ether is dried on anhydrous magnesium sulfate and evaporated to yield 2-methyl-1-(p-tolyl)propanol-1.
Workup
- additionThe reaction mixture is poured over ice
- extractionextracted with ether
- washThe ether solution is washed to neutrality
- customdried
- customevaporated
- distillationThe residue is distilled under diminished pressure
Sources & evidence
- ORD record
- ord-131fee7131fb458d9244863d195eb33a
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05292720
Reaction notes
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