Hydrochloric Acid → 2,2,3,3-Tetrafluoro-3-methoxypropanoic acid

HRID 370493Notes

Reaction equation

HRID 370493 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]([F:14])([F:13])[C:6]([F:12])([F:11])[C:7]([O:9]C)=[O:8].Cl>O>[CH3:3][O:4][C:5]([F:13])([F:14])[C:6]([F:11])([F:12])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69787Propanoic acid, 2,2,3,3-tetrafluoro-3-methoxy-, methyl ester

Product 1

HCID 133289072,2,3,3-Tetrafluoro-3-methoxypropanoic acidYield 73.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 32 g sodium hydroxide, 400 g water and 152 g methyl 3-methoxytetrafluoropropionate was stirred at room temperature until a single liquid layer was obtained. The product was acidified with 37% aqueous HCl and the lower layer separated. The aqueous layer was extracted four times with 50 ml ethyl ether and the combined ether extracts and lower layer distilled to give 103.3 g (73.4%) 3-methoxytetrafluoropropionic acid, b.p. 85°-86° at 20 mm.

Workup

  1. customwas obtained
  2. customthe lower layer separated
  3. extractionThe aqueous layer was extracted four times with 50 ml ethyl ether
  4. distillationthe combined ether extracts and lower layer distilled

Sources & evidence

ORD record
ord-55853faa2b874a40bf3a9ad4d06e07e0
Source dataset
uspto-grants-1985_07
Patent number
US04526948

Reaction notes

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