Methanol → HCID 66959475, compound

HRID 2063195Notes

Reaction equation

HRID 2063195 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[C:15]([S:16][CH3:17])=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:22]O>>[F:6][C:7]1[C:15]([S:16][CH3:17])=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=[CH:12][C:8]=1[C:9]([O:11][CH3:22])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 669577352-Fluoro-3-(methylthio)-4-(trifluoromethyl)benzoic acid

Product 1

HCID 66959475HCID 66959475, compound

Procedure

5 ml of concentrated sulfuric acid were added to 20.0 g (78.7 mmol) of 2-fluoro-3-methylthio-4-(trifluoromethyl)benzoic acid in 200 ml of methanol, and the mixture was heated under reflux until complete conversion had been achieved. The mixture was cooled and the solvent was removed. The residue was taken up in water, and the mixture was extracted twice with ethyl acetate. The combined organic phases were washed once with saturated aqueous NaHCO3 solution. Finally, the organic phase was dried and the filtrate was freed from the solvent. This gave 20.5 g of methyl 2-fluoro-3-methylthio-4-(trifluoromethyl)benzoate as residue.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux until complete conversion
  3. temperatureThe mixture was cooled
  4. customthe solvent was removed
  5. extractionthe mixture was extracted twice with ethyl acetate
  6. washThe combined organic phases were washed once with saturated aqueous NaHCO3 solution
  7. customFinally, the organic phase was dried

Sources & evidence

ORD record
ord-8815a8b68dee482eba2ef3f27c9a96ee
Source dataset
uspto-grants-2012_10
Patent number
US08288319B2

Reaction notes

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