(3-Isopropenyl-4-methoxyphenyl)acetonitrile → 3-Isopropyl-4-methoxyphenylacetonitrile

HRID 2076710Notes

Reaction equation

HRID 2076710 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH2:12][C:13]#[N:14])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])([CH3:3])=[CH2:2]>C(O)C.[C].[Pd]>[CH:1]([C:4]1[CH:5]=[C:6]([CH2:12][C:13]#[N:14])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67119142(3-Isopropenyl-4-methoxyphenyl)acetonitrile

Product 1

HCID 109103103-Isopropyl-4-methoxyphenylacetonitrileYield 91.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

(3-Isopropenyl-4-methoxyphenyl)acetonitrile (4.42 g, 23.61 mmol) obtained in Example (109-1) was dissolved in ethanol (50 ml) and 10% palladium-carbon (1 g) was added thereto, and the mixture was stirred at room temperature under a hydrogen atmosphere for 30 minutes. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1) to give (3-isopropyl-4-methoxyphenyl)acetonitrile (4.08 g, yield: 91%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue obtained
  4. customwas purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-2a9894b0e50c4b5d83e67b635829ac4b
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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