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

HRID 1378876Notes

Reaction equation

HRID 1378876 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].[H][H].C(OCC)(=O)C.CCCCCC>C(O)C.[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

6

Reactant 3

HCID 2584423-Allyl-4-hydroxybenzonitrileHCID 21226206Ethyl acetate hexaneHCID 178418361HCID 178418361, compound

Product 1

HCID 139876694-hydroxy-3-propylBenzonitrileYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A Parr hydrogenation shaker was charged with a solution of 29.76 g (187 mmol) of the product of Step A in 100 mL of ethanol and 3.00 g of a 10% palladium on carbon catalyst was added. The flask was mounted in the hydrogenation apparatus, freed of air, pressurized with hydrogen (40 psig) and shaken 80 minutes. At the end of this period, TLC analysis (15% ethyl acetate/hexane) indicated that the reaction was complete and the reaction mixture was filtered and evaporated. The product was dried in vacuo to afford 30.01 g (99%) of the title compound as a yellow oil.

Workup

  1. additionwas added
  2. filtrationthe reaction mixture was filtered
  3. customevaporated
  4. customThe product was dried in vacuo

Sources & evidence

ORD record
ord-8d81cb0521dd4118b4af26255d8d55cb
Source dataset
uspto-grants-1997_09
Patent number
US05668176

Reaction notes

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