2-Cyclohexen-1-one, 4,4-dimethyl- → Cyclohexanone, 4,4-dimethyl-

HRID 70263

Reaction equation

HRID 70263 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=[O:8])[CH:4]=[CH:3]1>CCOC(C)=O.[Pd]>[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 1368392-Cyclohexen-1-one, 4,4-dimethyl-

Product 1

HCID 138166Cyclohexanone, 4,4-dimethyl-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4,4-dimethyl-2-cyclohexene-1-one (5.5 g) and 10% Pd/C (0.25 g, wet, Degussa type E101) in EtOAc (50 mL) was hydrogenated under 15 psi for 3 h at room temperature. The mixture was filtered through Celite and the filtrate was concentrated in vacuo affording the title compound as a colorless solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.07 (s, 6H), 1.65 (t, J=7 Hz, 4H), 2.35 (t, J=7 Hz, 4H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ebc8b3ee3a4e4f728cceb2cefb9e3d3b
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Linked notes

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