p-Toluenesulfonic acid → Ethyl 6,6,6-trifluoro-3-oxohexanoate

HRID 1079022Notes

Reaction equation

HRID 1079022 reaction equation
[F:1][C:2]([F:15])([F:14])[CH2:3][CH2:4][C:5]([CH:7]([C:11]([OH:13])=[O:12])C(O)=O)=[O:6].[C:16]1(C)C=CC(S(O)(=O)=O)=C[CH:17]=1.C(=O)([O-])O.[Na+]>O>[F:15][C:2]([F:1])([F:14])[CH2:3][CH2:4][C:5]([CH2:7][C:11]([O:13][CH2:16][CH3:17])=[O:12])=[O:6]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 189709114,4,4-Trifluorobutyrylmalonic acid

Product 1

HCID 18970913Ethyl 6,6,6-trifluoro-3-oxohexanoateYield 24,903.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 179 g of the 4,4,4-trifluorobutyrylmalonic acid ditheyl ester thus obtained, 260 ml of water and 322 mg of p-toluenesulfonic acid was refluxed with vigorous stirring for 6 hours. The reaction solution was then poured into saturated aqueous sodium hydrogencarbonate solution and extracted three times with diethyl ether. The ether layers were combined and the combined layer was washed with brine, dried over anhydrous magnesium sulfate. After the drying agent was removed, the solvent was removed under reduced pressure. The obtained residue was distilled inder reduced pressure to yield 98.8 g of the desired ethyl 4,4,4-trifluorobutyrylacetate in a yield of 74%.

Workup

  1. customthus obtained
  2. extractionextracted three times with diethyl ether
  3. washthe combined layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the drying agent was removed
  6. customthe solvent was removed under reduced pressure
  7. distillationThe obtained residue was distilled inder reduced pressure

Sources & evidence

ORD record
ord-14b67357ee6d4d22a27ae8c54587bce1
Source dataset
uspto-grants-1996_08
Patent number
US05550258

Reaction notes

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