4-(4-Hydroxybut-1-yn-1-yl)benzonitrile → 4-(4-Hydroxybutyl)benzonitrile

HRID 1351130Notes

Reaction equation

HRID 1351130 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][CH2:11][CH2:12][OH:13])=[CH:5][CH:4]=1)#[N:2].[H][H]>C(O)C.[Pd]>[OH:13][CH2:12][CH2:11][CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 230795014-(4-Hydroxybut-1-yn-1-yl)benzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 185403804-(4-Hydroxybutyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(4-Cyanophenyl)but-3-yn-1-ol (40 g, 1 wt eq, see step (i) above) in ethanol (200 mL, 5 vol) and palladium on charcoal (20 g, 0.5 wt eq, 10% Johnson Matthey type 487, 60% water) were stirred rapidly under five bar hydrogen pressure for five hours. The reaction was monitored by HPLC for the disappearance of the starting material, and the formation of sub-title compound. The reaction was filtered through kieselguhr and washed with ethanol (80 mL, 2 vol). The ethanol solution was concentrated in vacuo to give sub-title alcohol as a yellow-brown oil. Yield 36.2g, 88.5%.

Sources & evidence

ORD record
ord-e32cc1da64a34e87b272180b56096742
Source dataset
uspto-grants-2007_05
Patent number
US07217708B2

Reaction notes

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