Dimedone → 5,5-Dimethylcyclohexane-1,3-diol
Reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[CH2:3]1.[BH4-].[Na+].CO.O>C1COCC1>[CH3:1][C:2]1([CH3:10])[CH2:3][CH:4]([OH:5])[CH2:6][CH:7]([OH:8])[CH2:9]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
14.0 g (0.1 mol) of dimedone were dissolved in 200 ml of THF. 3.8 g (0.1 mol) of NaBH4 and 5 mmol of CeCl3 dissolved in 50 ml of THF were then added at -30° C. The mixture was stirred at room temperature for another 2 hours and was hydrolyzed at 0° C. by means of methanol/water. The organic phase was separated off and the solvent was removed. The residue was extracted with ethanol and unreacted dimedone was removed by crystallization. This gave 11.5 g (80%) of 5,5-dimethylcyclohexane-1,3-diol.
Workup
- additionwere then added at -30° C
- customThe organic phase was separated off
- customthe solvent was removed
- extractionThe residue was extracted with ethanol and unreacted dimedone
- customwas removed by crystallization
Sources & evidence
- ORD record
- ord-af0ea399c8674ba7b628a1320df87b8f
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06077965
Reaction notes
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