Hydrochloric Acid → 4,4,4-Trifluoro-1-(3-methyl-4-methoxylphenyl)-1,3-butanedione

HRID 1860586Notes

Reaction equation

HRID 1860586 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[F:13][C:14]([F:21])([F:20])[C:15](OCC)=[O:16].C[O-].[Na+].Cl>COCCOC.O.CCOC(C)=O>[F:13][C:14]([F:21])([F:20])[C:15](=[O:16])[CH2:11][C:10]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([CH3:1])[CH:3]=1)=[O:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 248061-(4-Methoxy-3-methylphenyl)ethan-1-oneHCID 10942334Sodium Methoxide

Product 1

HCID 113912984,4,4-Trifluoro-1-(3-methyl-4-methoxylphenyl)-1,3-butanedioneYield 62%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To stirred solution of 1-(3-methyl-4-methoxyphenyl)ethanone (3.29 g, 20 mmol) in DME was added ethyl trifluoroacetate (5.68 g, 40 mmol) and sodium methoxide (4.32 g, 80 mmol), and the resulting reaction mixture was stirred at room temperature overnight. EtOAc (200 ml) and water (50 ml) were added, and the pH of the aqueous layer was adjusted to 6 by addition of 1 N HCl solution. The organic layer was washed with brine (50 ml), dried over Na2SO4, and concentrated in vacuo to give the crude product which was recrystallized from isooctane to give the title compound (3.2 g, 62%).

Workup

  1. customthe resulting reaction mixture
  2. washThe organic layer was washed with brine (50 ml)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give the crude product which
  6. customwas recrystallized from isooctane

Sources & evidence

ORD record
ord-085c6ab1ed834103b05cdb48ea8d3aeb
Source dataset
uspto-grants-2003_03
Patent number
US06531492B1

Reaction notes

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