Majantol → 2,2-Dimethyl-3-(3-methylcyclohexyl)propan-1-ol
Reaction equation
[CH3:1][C:2]([CH3:13])([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[CH:7]=1)[CH2:3][OH:4]>O.[Rh]>[CH3:1][C:2]([CH3:13])([CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH:8]([CH3:12])[CH2:7]1)[CH2:3][OH:4]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
5% Rh/C (450 mg, 15% w/w) was charged into a 50 mL autoclave vessel containing a mixture of 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol (6 g, 34 mmol) in water (17 mL). The mixture was vigorously stirred under an hydrogen atmosphere (10 Bar) at 60° C. for 6 h. The reaction mixture was filtered and the filtrate was extracted with MTBE (25 mL), dried over magnesium sulphate and concentrated. The resulting crude product was distilled with a bulb-to-bulb distillation (2.5 mBar, 90° C.) to give 2,2-dimethyl-3-(3-methylcyclohexyl)propan-1-ol (5.1 g, gc purity>99%; yield 82%).
Workup
- additioncontaining
- filtrationThe reaction mixture was filtered
- extractionthe filtrate was extracted with MTBE (25 mL)
- dry with materialdried over magnesium sulphate
- concentrationconcentrated
- distillationThe resulting crude product was distilled with a bulb-to-bulb distillation (2.5 mBar, 90° C.)
Sources & evidence
- ORD record
- ord-beb4fec26d5f494e9bee0fa0dfd974a8
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08709994B2
Reaction notes
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