Hydrochloric Acid → 4-(4-Methylphenyl)butan-2-ol
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=[O:12])[CH3:11])=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]([OH:12])[CH3:11])=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1-(4-methylphenyl)butan-3-one (11.4 g, 70.3 mmol) in methanol (80 ml) was cooled, followed by adding thereto sodium tetrahydroborate (1.51 g, 40.0 mmol), and the resulting mixture was stirred at 0° C. for 2 hours. The reaction mixture was added to 1N hydrochloric acid, and the methanol was distilled off under reduced pressure and the residue was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 11.7 g of 1-(4-methylphenyl)butan-3-ol.
Workup
- additionby adding
- distillationthe methanol was distilled off under reduced pressure
- extractionthe residue was extracted with ethyl acetate
- washThe extract solution was washed with a saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-5eb543cb27fb44b0b542c21fdd42519d
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06369110B1
Reaction notes
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