2-(3-Ethoxy-buta-1,3-dienyl)-5-hydroxy-benzonitrile → 2-(3-Ethoxy-but-3-enyl)-5-hydroxy-benzonitrile

HRID 1181099Notes

Reaction equation

HRID 1181099 reaction equation
[CH2:1]([O:3][C:4](=[CH2:16])[CH:5]=[CH:6][C:7]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:8]=1[C:9]#[N:10])[CH3:2].[H][H]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4](=[CH2:16])[CH2:5][CH2:6][C:7]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:8]=1[C:9]#[N:10])[CH3:2]

Participants

5

Reactant 2

HCID 734148902-(3-Ethoxy-buta-1,3-dienyl)-5-hydroxy-benzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 179843252-(3-Ethoxy-but-3-enyl)-5-hydroxy-benzonitrileYield 67.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(3-ethoxy-buta-1,3-dienyl)-5-hydroxy-benzonitrile (600 mg) in EtOAc (50 mL) was added 5% Pd/C (0.3 g). The reaction was exposed to hydrogen gas in a Parr apparatus at 60 psi overnight at ambient temperature. The reaction mixture was filtered and concentrated to give the title compound (410 mg). MS [EI] m/z 218 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5d1d6830a90a4804bb6a4b5e3cb9848d
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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