Water → trans-4-(trans-4-Propylcyclohexyl)cyclohexanol
Reaction equation
[H-].[Na+].[CH:3]1([OH:15])[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:5][CH2:4]1.[CH2:16](Br)[CH2:17][CH3:18].O>CN(C)C=O>[CH2:16]([CH:12]1[CH2:13][CH2:14][CH:9]([CH:6]2[CH2:5][CH2:4][CH:3]([OH:15])[CH2:8][CH2:7]2)[CH2:10][CH2:11]1)[CH2:17][CH3:18]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
60% Sodium hydride (1.01 g) was added slowly to a suspension of 4,4′-bicyclohexanol (5 g) in N,N-dimethylformamide (50 ml) at ambient temperature, and the mixture was stirred for 6 hours at 80° C. To the mixture was added dropwise n-propylbromide (2.29 ml) at 0-5° C., and the reaction mixture was stirred for 18.5 hours at 80° C. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with brine and dried, and the solvent was evaporated under reduced pressure. The residue was chromatographed on a column of silica gel eluting with dichloromethane/methyl alcohol (50:1) to give 4′-propyl-4-hydroxy-1,1′-bicyclohexane (1.21 g).
Workup
- stirringthe reaction mixture was stirred for 18.5 hours at 80° C
- extractionextracted with ethyl acetate
- washThe organic layer was washed with brine
- customdried
- customthe solvent was evaporated under reduced pressure
- customThe residue was chromatographed on a column of silica gel eluting with dichloromethane/methyl alcohol (50:1)
Sources & evidence
- ORD record
- ord-4626668acc8f477390a4547eaad91876
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06884868B1
Reaction notes
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