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

HRID 229142Notes

Reaction equation

HRID 229142 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=[O:8])[CH:4]=[CH:3]1>[Pd].CCOC(C)=O>[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 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared according to the method described by H-J Liu, et al., (Can. J. Chem. (1988), 66, 2345) with modification. To a three-neck round-bottomed flask was added palladium on carbon (Degussa Type, 10% wt. (dry basis)) (0.167 g). The flask was evacuated and then filled with nitrogen and the evacuation/fill cycle was repeated twice more. To the flask was added a solution of 4,4-dimethyl-2-cyclohexene-1-one (2.1 mL, 2.0 g, 16 mmol) in EtOAc (100 mL). The flask was evacuated and then filled with nitrogen and the evacuation/fill cycle was repeated once more. The flask was evacuated and then filled with hydrogen using a balloon. The reaction mixture was stirred under a hydrogen atmosphere at room temperature overnight. The flask was evacuated and filled with nitrogen. The reaction mixture was filtered through a pad of Celite and the pad was washed with EtOAc. The filtrate was concentrated to give 1.63 g (82%) of compound 20 as a colorless liquid that solidified to a white solid. 1H NMR is consistent with that reported in the cited reference. 1H NMR (400 MHz, CDCl3): δ 1.08 (s, 6H), 1.65 (t, J=6.9 Hz, 4H), 2.33 (t, J=6.9 Hz, 4H).

Workup

  1. customThis compound was prepared
  2. customThe flask was evacuated
  3. additionfilled with nitrogen
  4. customThe flask was evacuated
  5. additionfilled with nitrogen
  6. customThe flask was evacuated
  7. additionfilled with hydrogen using a balloon
  8. customThe flask was evacuated
  9. additionfilled with nitrogen
  10. filtrationThe reaction mixture was filtered through a pad of Celite
  11. washthe pad was washed with EtOAc
  12. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1406d8cc59f34ee0872930e6db71d5e3
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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