Butanal → 2-Butyl-5-methoxy-1-indanone

HRID 2113641Notes

Reaction equation

HRID 2113641 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[CH2:9][CH2:8]2.[CH:15](=O)[CH2:16][CH2:17][CH3:18]>[Pd].C(O)C>[CH2:15]([CH:9]1[CH2:8][C:7]2[C:11](=[CH:12][CH:13]=[C:5]([O:4][CH3:3])[CH:6]=2)[C:10]1=[O:14])[CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 261ButanalHCID 14797Potassium HydroxideHCID 787875-Methoxyindan-1-one

Product 1

HCID 120457522-Butyl-5-methoxy-1-indanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Potassium hydroxide (0.44 g, 85% weight pure, 6.67 mmol) and 10% palladium on activated carbon (0.42 g) were added to a mixture of 5-methoxy-1-indanone (5.0 g, 30.8 mmol) and butyraldehyde (3.3 mL, 37 mmol) in ethanol (30 mL). The resulting mixture was stirred under an atmosphere of hydrogen at room temperature for 2 hours. The mixture was filtered and the filtrate evaporated under vacuum. The residue was partitioned between EtOAc (200 mL) and water (200 mL) containing 2N HCl (5 mL). The organic phase was washed with brine (100 mL), dried over MgSO4, filtered, and evaporated under vacuum to afford crude 2-butyl-5-methoxy-1-indanone as an oil.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated under vacuum
  3. customThe residue was partitioned between EtOAc (200 mL) and water (200 mL)
  4. additioncontaining 2N HCl (5 mL)
  5. washThe organic phase was washed with brine (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-e7040b6ff74a4408a6f1c58338ebb1b6
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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