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

HRID 7823

Reaction equation

HRID 7823 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-indanoneYield 104.1%

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 (7.0 g) 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-92a03a8e4c1e41349e525d8248b38466
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Linked notes

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