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

HRID 865547Notes

Reaction equation

HRID 865547 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 appartus, freed of air, pressurized with hydrogen (40 psig) and shaken 80 minutes. At the end of this preiod, 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-ac7037940627436d94a0c8b14635c28f
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Reaction notes

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