Methanol → 2-(4-Chlorophenoxy)-3,3,3-trifluoro-2-(trifluoromethyl)propanoic acid

HRID 2419913Notes

Reaction equation

HRID 2419913 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]([C:17]([F:20])([F:19])[F:18])([C:13]([F:16])([F:15])[F:14])[C:8]([O:10]CC)=[O:9])=[CH:4][CH:3]=1.[OH-].[K+].CO>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]([C:13]([F:14])([F:15])[F:16])([C:17]([F:20])([F:19])[F:18])[C:8]([OH:10])=[O:9])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 13384231HCID 13384231, compound

Product 1

HCID 133842322-(4-Chlorophenoxy)-3,3,3-trifluoro-2-(trifluoromethyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 2-(4-chlorophenoxy)-3,3,3-trifluoro-2-trifluoromethylpropionate (14.6 g.), 4.5 N-aqueous potassium hydroxide (19.2 ml.) and methanol (35 ml.) is stirred at ambient temperature for 21/4 hours. The resulting solution is diluted with water and washed with ether. The aqueous phase is acidified with concentrated hydrochloric acid, and extracted with ether. The extract is washed with water, dried with sodium sulphate and evaporated. The residue is sublimed twice at 100° C. and 0.3 mm. pressure, and the sublimate is washed with light petroleum (b.p. 30°-40° C.) to give (2-(4-chlorophenoxy)-3,3,3-trifluoro-2-trifluoromethylpropionic acid, m.p. 81°-83° C. (5.1 g.). The acid may be further purified by crystallisation (prisms) from light petroleum (b.p. 60°-80° C.) followed by sublimation, which yields material of m.p. 82°-83° C.

Workup

  1. washwashed with ether
  2. extractionextracted with ether
  3. washThe extract is washed with water
  4. dry with materialdried with sodium sulphate
  5. customevaporated
  6. customis sublimed twice at 100° C.
  7. washpressure, and the sublimate is washed with light petroleum (b.p. 30°-40° C.)

Sources & evidence

ORD record
ord-51e32aafe82346c49f849fcf0c85d513
Source dataset
uspto-grants-1978_08
Patent number
US04107329

Reaction notes

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