Water → 1,2,2a,3,4,5-Hexahydroacenaphthylen-1-ol
Reaction equation
[C:1]1(=[O:13])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1.[BH4-].[Na+].O>CO>[CH:1]1([OH:13])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2a,3,4,5-Tetrahydro-2H-acenaphthylen-1-one (4.85 g) was dissolved in methanol (70 ml). Sodium borohydride (1.07 g) was added to the solution under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over magnesium sulfate, and concentrated to give 2a,3,4,5-tetrahydro-2H-acenaphthylen-1-ol.
Workup
- temperaturecooling
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with water and saturated brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-cb3f040aaf2d4d52aeaa7a6e7014f502
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877779B2
Reaction notes
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