Potassium Carbonate → 9-Phenylnonan-2-one

HRID 1603644Notes

Reaction equation

HRID 1603644 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:14]([CH2:17]C(=O)C)(=[O:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:8]1([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:15][C:14](=[O:16])[CH3:17])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31261AcetylacetoneHCID 145296726-Phenyl-1-hexyl iodide

Product 1

HCID 187819999-Phenylnonan-2-oneYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Iodo-1-phenylhexane (17.43 g, 0.061 mol), acetyl acetone (6.66 g, 0.067) and potassium carbonate (8.41 g, 0.061 mol) were dissolved in dry absolute ethanol (75 ml) and the solution was refluxed for 18 hours. After cooling to room temperature the solution was filtered and evaporated under reduced pressure to an oil. This was partitioned between ethyl acetate (80 ml) and water (80 ml), and the organic layer was washed with brine, dried and evaporated to an orange oil (15.27 g). This was purified by flash chromatography on silica gel using petroleum ether/ethyl acetate to give 9-phenylnonan-2-one as a colourless oil (7.12 g, 54%).

Workup

  1. temperaturethe solution was refluxed for 18 hours
  2. filtrationwas filtered
  3. customevaporated under reduced pressure to an oil
  4. customThis was partitioned between ethyl acetate (80 ml) and water (80 ml)
  5. washthe organic layer was washed with brine
  6. customdried
  7. customevaporated to an orange oil (15.27 g)
  8. customThis was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-158a1d0d55214536b7d0394dcf2d5175
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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