4,4-Diethylcyclohex-2-en-1-one → 4,4-Diethylcyclohexan-1-one

HRID 1924814Notes

Reaction equation

HRID 1924814 reaction equation
[CH2:1]([C:3]1([CH2:10][CH3:11])[CH2:8][CH2:7][C:6](=[O:9])[CH:5]=[CH:4]1)[CH3:2]>CC(=O)OCC.[Pd]>[CH2:10]([C:3]1([CH2:1][CH3:2])[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)[CH3:11]

Participants

4

Reactant 1

HCID 124849234,4-Diethylcyclohex-2-en-1-one

Product 1

HCID 148363144,4-Diethylcyclohexan-1-oneYield 107.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4,4-diethyl-cyclohex-2-enone (10.7 g, 70.5 mmol) in EA (400 mL) is treated with Pd/C (1.0 g, 10% Pd). The suspension is stirred at rt for 24 h under 1 bar of H2. The mixture is filtered, and the filtrate is evaporated to give 4,4-diethyl-cyclohexanone (11.7 g) as a colourless solid; 1H NMR (CD3OD): δ 2.32 (t, J=7.0 Hz, 4H), 1.66 (t, J=7.0 Hz, 4H), 1.48 (q, J=7.6 Hz, 4H), 0.88 (t, J=7.6 Hz, 6H).

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-41e40fa13a8244b18044abea56d368b6
Source dataset
uspto-grants-2012_05
Patent number
US08178562B2

Reaction notes

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