Water → Ethyl 3-difluoromethoxy-2,4,5-trifluorobenzoylacetate

HRID 2226486Notes

Reaction equation

HRID 2226486 reaction equation
[F:1][CH:2]([F:26])[O:3][C:4]1[C:5]([F:25])=[C:6]([CH:20]=[C:21]([F:24])[C:22]=1[F:23])[C:7]([CH:9](C(OCC)=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:8].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(=O)(O)[O-].[Na+]>O1CCOCC1>[F:26][CH:2]([F:1])[O:3][C:4]1[C:5]([F:25])=[C:6]([CH:20]=[C:21]([F:24])[C:22]=1[F:23])[C:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 15023783Diethyl 3-difluoromethoxy-2,4,5-trifluorobenzoylmalonate

Product 1

HCID 15023784Ethyl 3-difluoromethoxy-2,4,5-trifluorobenzoylacetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The whole of the diethyl 3-difluoromethoxy-2,4,5-trifluorobenzoylmalonate [(XIV), R1 =--OCHF2, R3' =H, R17 =C2H5, X=X'=F] [prepared as described in step (a) above] was dissolved in 200 ml of dioxane, and then 4.52 g (0.0238 moles) of p-toluene-sulfonic acid monohydrate were added to the resulting solution. The mixture was then heated under reflux for 6 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure. 100 ml of water and 2.52 g (0.03 moles) of sodium bicarbonate were added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure to give 5.66 g of ethyl 3-difluoromethoxy-2,4,5-trifluorobenzoylacetate as a reddish brown liquid.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 6 hours
  3. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-f20a67c54fe3426ab41b5d584353a8db
Source dataset
uspto-grants-1994_09
Patent number
US05348961

Reaction notes

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