4-(2-Hydroxypropan-2-yl)benzonitrile → 2-[4-(Aminomethyl)phenyl]propan-2-ol
Reaction equation
[OH:1][C:2]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:10][CH2:9][C:8]1[CH:11]=[CH:12][C:5]([C:2]([OH:1])([CH3:3])[CH3:4])=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 4-(1-hydroxy-1-methyl-ethyl)-benzonitrile (1.4 g, 8.7 mmol) in tetrahydrofuran (26 ml) at 0° C. was added a solution of 1.0 M lithium aluminum hydride (26 ml, 26.1 mmol). The reaction mixture was refluxed for 30 minutes, cooled to 0° C., and then quenched with methanol added drop-wise. The reaction mixture was thereafter poured into chloroform (300 ml), washed with water (80 ml), dried over magnesium sulfate (MgSO4), and concentrated to give 1.1 g 2-(4-aminomethyl-phenyl)-propan-2-ol as a white solid, mp 62-4° C.
Workup
- temperatureThe reaction mixture was refluxed for 30 minutes
- customquenched with methanol added drop-wise
- additionThe reaction mixture was thereafter poured into chloroform (300 ml)
- washwashed with water (80 ml)
- dry with materialdried over magnesium sulfate (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d66429df5778488186357c9e04e823da
- Source dataset
- uspto-grants-2004_05
- Patent number
- US06740655B2
Reaction notes
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