Methyl 2-(Trifluoromethyl)-3,3,3-trifluoropropionate → Methyl 3,3,3-trifluoropropanoate

HRID 1979812

Reaction equation

HRID 1979812 reaction equation
C([O-])(=O)C.[K+].[F:6][C:7]([F:18])([F:17])[CH:8](C(F)(F)F)[C:9]([O:11][CH3:12])=[O:10]>O>[F:6][C:7]([F:18])([F:17])[CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 9673Methyl 2-(Trifluoromethyl)-3,3,3-trifluoropropionateHCID 517044Potassium Acetate

Product 1

HCID 2782392Methyl 3,3,3-trifluoropropanoateYield 76.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 150 g (1.5 mol) of potassium acetate in 500 ml of water was added dropwise to a solution of 105 g (0.5 mol) of methyl 2-(trifluoromethyl)-3,3,3-trifluoropropionate as above produced in 250 ml of water and the mixture was refluxed for 5 hours. After separation of the oily layer, extraction was made from the water layer that was left with use of methylene chloride and the solution of extracts and separated oily layer were joined and dried. After methylene chloride was removed by evaporation under atmospheric pressure, purification was made by distillation to give methyl 3,3,3-trifluoropropionate (TFPE) (54.07 g, 76%). Its analysis gave the following data:

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. customAfter separation of the oily layer, extraction
  3. waitwas left with use of methylene chloride
  4. customthe solution of extracts and separated oily layer
  5. customdried
  6. customAfter methylene chloride was removed by evaporation under atmospheric pressure, purification
  7. distillationwas made by distillation

Sources & evidence

ORD record
ord-1282e9b3402f4933bea6537a1f0404ba
Source dataset
uspto-grants-1984_11
Patent number
US04482729

Linked notes

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