2,6-Lutidine → 4-Methylcyclohexane-1-carbaldehyde

HRID 2410124Notes

Reaction equation

HRID 2410124 reaction equation
N1[C:6]([CH3:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].C1C[O:12][CH2:11]C1>[Pd]>[CH3:8][CH:2]1[CH2:7][CH2:6][CH:5]([CH:11]=[O:12])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 79372,6-LutidineHCID 8028Tetrahydrofuran

Product 1

HCID 138394374-Methylcyclohexane-1-carbaldehyde

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of the compound prepared in step 115.6 (8.8 g, 54.7 mmol) and Pd/C 10% (5.8 g, 54.7 mmol) in THF (150 mL) and 2,6-lutidine (11.7 g, 109 mmol) was stirred for 15.5 h at rt, under a hydrogen atmosphere. The reaction mixture was filtered through a pad of celite. The crude was dissolved in CH2Cl2 and extracted with 1N HCl then with a saturated aqueous NaHCO3 solution. The organic layer was dried (Na2SO4), filtered and concentrated.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. dissolutionThe crude was dissolved in CH2Cl2
  3. extractionextracted with 1N HCl
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dbb8e343a3284473ac7e5bf784ae4e69
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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