4'-Methoxyacetophenone → 1-(4-Methoxyphenyl)butane-1,3-dione

HRID 2261758Notes

Reaction equation

HRID 2261758 reaction equation
[H-].[Na+].[C:3](OCC)(=[O:5])[CH3:4].[CH3:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:11]>C1COCC1.C(O)C.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10](=[O:11])[CH2:9][C:3](=[O:5])[CH3:4])=[CH:13][CH:14]=1

Participants

7

Reactant 3

HCID 74764'-MethoxyacetophenoneHCID 8857Ethyl AcetateHCID 24758Sodium hydride

Product 1

HCID 776401-(4-Methoxyphenyl)butane-1,3-dioneYield 81%

Reagents, catalysts & solvents 3

HCID 702EthanolCatalystHCID 26541Dibenzo-18-crown-6CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. suspension of sodium hydride (853 mg, 21.8 mmol, 60% oil dispersion) in THF (13 mL) is added ethyl acetate (2.03 mL, 20.8 mmol). The reaction is stirred at room temperature for 1 h. A solution of 4-methoxyacetophenone (1.56 g, 10.4 mmol), dibenzo-18-crown-6 (62 mg, 0.016 mmol) and ethanol (2 drops) in THF (13 mL) is added dropwise and the reaction mixture is heated to reflux. After 3 h, the reaction is cooled to room temperature, quenched with saturated aqueous NH4Cl, and concentrated under reduced pressure. The residue is partitioned between EtOAc (200 mL) and water (50 mL). The aqueous layer is extracted with EtOAc (200 mL) and the combined organic layers are washed with brine, dried (MgSO4), filtered, and concentrated. The residue is purified via chromatography (0 to 20% EtOAc/Hexanes) to yield the title compound (1.62 g, 81%). GC-ES/MS m/e 192

Workup

  1. temperaturethe reaction mixture is heated to reflux
  2. waitAfter 3 h
  3. temperaturethe reaction is cooled to room temperature
  4. customquenched with saturated aqueous NH4Cl
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is partitioned between EtOAc (200 mL) and water (50 mL)
  7. extractionThe aqueous layer is extracted with EtOAc (200 mL)
  8. washthe combined organic layers are washed with brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue is purified via chromatography (0 to 20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-f00bc8dba5ef4e46958f05b5c67e6240
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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