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

HRID 1924808Notes

Reaction equation

HRID 1924808 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=[O:8])[CH:4]=[CH:3]1>CC(=O)OCC.[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-Yield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 4,4-dimethyl-cyclohex-2-enone (50 g, 403 mmol) in EA (230 mL), a suspension of Pd/C (2.5 g, 10% Pd) in EA is added. The suspension is stirred at rt for 2 h under 1 bar H2. The catalyst is filtered off and the solvent of the filtrate is carefully evaporated to give 4,4-dimethyl-cyclohexanone (50 g) as a colourless oil which slowly crystallizes; 1H NMR (CDCl3): δ 2.34 (t, J=6.4 Hz, 4H), 1.66 (t, J=6.4 Hz, 4H), 1.09 (s, 6H).

Workup

  1. additionis added
  2. filtrationThe catalyst is filtered off
  3. customthe solvent of the filtrate is carefully evaporated

Sources & evidence

ORD record
ord-0be8db7542f2459e9d464838a7534f6a
Source dataset
uspto-grants-2012_05
Patent number
US08178562B2

Reaction notes

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