3-Allyl-4-hydroxybenzonitrile → 4-hydroxy-3-propylBenzonitrile

HRID 2424949Notes

Reaction equation

HRID 2424949 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

HCID 2584423-Allyl-4-hydroxybenzonitrile

Product 1

HCID 139876694-hydroxy-3-propylBenzonitrileYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Allyl-4-hydroxybenzonitrile (20.0 g, 126 mmol) (Example 32) 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

  1. filtrationThe catalyst was filtered off
  2. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3ca116eaaca24133969279dafac8db33
Source dataset
uspto-grants-2011_06
Patent number
US07964622B2

Reaction notes

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