Acetic Acid → 2-Methoxy-4-trifluoromethanesulfonyloxybenzoic acid

HRID 2243521Notes

Reaction equation

HRID 2243521 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])[CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].S(=O)(=O)(O)O.C(O)(=O)C>O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][S:14]([C:17]([F:20])([F:18])[F:19])(=[O:16])=[O:15])[CH:10]=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 23282575Methyl 2-methoxy-4-trifluoromethane-sulfonyloxybenzoate

Product 1

HCID 231343522-Methoxy-4-trifluoromethanesulfonyloxybenzoic acidYield 37.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of methyl 2-methoxy-4-trifluoromethane-sulfonyloxybenzoate (3.49 g), sulfuric acid (90%, 0.1 mL), acetic acid (10 mL) and water (2 mL) was heated under reflux for 16 hrs. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over an hydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by recrystallization (solvent: ethyl acetate/n-hexane) to afford the title compound (1.25 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over an hydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by recrystallization (solvent: ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-aafc8c027b5b4da2b53de7266f47d3f5
Source dataset
uspto-grants-2010_03
Patent number
US07674938B2

Reaction notes

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