Hydrochloric Acid → 2-Methylthio-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid

HRID 4748Notes

Reaction equation

HRID 4748 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[C:7]([C:9]([OH:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:5][C:4]=1[CH2:19][CH2:20][C:21]([O:23]C)=[O:22].Cl>[OH-].[Na+]>[CH3:1][S:2][C:3]1[CH:8]=[C:7]([C:9]([OH:18])([C:10]([F:11])([F:12])[F:13])[C:14]([F:16])([F:17])[F:15])[CH:6]=[CH:5][C:4]=1[CH2:19][CH2:20][C:21]([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131715455HCID 131715455, compound

Product 1

HCID 201518432-Methylthio-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3,4-dihydro-7-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-2H-1-benzothiapyran-2-one in dimethylacetamide can be added a one molar excess of sodium hydroxide in methanol. The resulting solution should be heated, and a one molar excess of methyl iodide should be added with stirring. From the resulting reaction mixture can be isolated 2-methylthio-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid, methyl ester. This ester should be dissolved in an aqueous solution of sodium hydroxide to obtain a solution which will be heated on a steam bath. Concentrated hydrochloric acid can then be added to this solution, thereby yielding a precipitate which can be isolated to give 2-methylthio-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid.

Workup

  1. customto obtain a solution which
  2. temperaturewill be heated on a steam bath
  3. customyielding a precipitate which
  4. customcan be isolated

Sources & evidence

ORD record
ord-2f5977fcdfc64a0bba0973c2c4fe06ab
Source dataset
uspto-grants-1988_02
Patent number
US04727180

Reaction notes

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