3-Allyl-4-hydroxybenzonitrile → 4-hydroxy-3-propylBenzonitrile
Reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[C:7]#[N:8])[CH:2]=[CH2:3]>CCO.[Pd]>[OH:12][C:11]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[CH2:1][CH2:2][CH3:3]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
3-Allyl-4-hydroxybenzonitrile (20.0 g, 126 mmol) (Example 28) was dissolved in EtOH (320 mL) under argon. Pd/C (80 mg, 10%, Fluka) was added, and the reaction mixture was stirred under a hydrogen atmosphere (1 atm) at rt for 20 h. The catalyst was filtered off, and then the reaction mixture was concentrated under reduced pressure, yielding 20.2 g (99%) of the title compound as a slightly greenish oil. 1H NMR (400 MHz, CDCl3): 0.95 (t, 3H), 1.63 (m, 2H), 2.56 (m, 2H), 6.86 (d, 1H), 7.30 (m, 2H).
Workup
- filtrationThe catalyst was filtered off
- concentrationthe reaction mixture was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-8c1cb3ebd585407a82d09566222bfb9f
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07906653B2
Reaction notes
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