p-METHYLACETOPHENONE → 4,4,4-Trifluoro-1-(4-methylphenyl)butane-1,3-dione

HRID 1941685Notes

Reaction equation

HRID 1941685 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C[O-].[Na+].[F:14][C:15]([F:22])([F:21])[C:16](OCC)=[O:17]>CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH2:9][C:16](=[O:17])[C:15]([F:22])([F:21])[F:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8500p-METHYLACETOPHENONEHCID 9794Ethyl trifluoroacetateHCID 10942334Sodium Methoxide

Product 1

HCID 5501934,4,4-Trifluoro-1-(4-methylphenyl)butane-1,3-dioneYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4′-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4×75 mL ethyl acetate. The extracts were dried over MgSO4, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.

Workup

  1. temperatureAfter refluxing for 24 hours
  2. concentrationconcentrated
  3. addition100 mL 10% HCl was added
  4. extractionthe mixture extracted with 4×75 mL ethyl acetate
  5. dry with materialThe extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b22861604e8e4982808924fed117f64c
Source dataset
uspto-grants-2013_03
Patent number
USRE044048E1

Reaction notes

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