4-(4-Oxo-cyclohex-1-enyl)-benzonitrile → 4-(4-Oxocyclohexyl)benzonitrile

HRID 475695Notes

Reaction equation

HRID 475695 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[CH:4][CH2:3]1>CCOC(C)=O.[Pd]>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 578925874-(4-Oxo-cyclohex-1-enyl)-benzonitrile2×

Product 1

HCID 157899134-(4-Oxocyclohexyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the crude mixture of 4-(4-oxo-cyclohex-1-enyl)-benzonitrile and 4-(4-oxo-cyclohex-1-enyl)-benzonitrile prepared above in step c (36.6 mmol) in EtOAc (120 mL) was added 10% Pd—C (900 mg) and the reaction was degassed (3×vacuum and H2). After being stirred 7 hours under H2 atmosphere, additional 10% Pd—C (500 mg) was added and the resulting reaction was stirred for an additional 12 h under H2 atmosphere. The catalyst was removed by filtration through Celite and the filtrate was concentrated under reduced pressure to give 4-(4-oxo-cyclohexyl)-benzonitrile as a white solid. The product was used for next step without further purification.

Workup

  1. customthe reaction was degassed (3×vacuum and H2)
  2. additionadditional 10% Pd—C (500 mg) was added
  3. customthe resulting reaction
  4. stirringwas stirred for an additional 12 h under H2 atmosphere
  5. customThe catalyst was removed by filtration through Celite
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-89b94985e2d54032b538a9db320c4123
Source dataset
uspto-grants-2014_01
Patent number
US08637576B2

Reaction notes

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