Acetic Acid → 2-Methoxy-4-trifluoromethanesulfonyloxybenzoic acid

HRID 2220617Notes

Reaction equation

HRID 2220617 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-trifluoromethanesulfonyloxybenzoate (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 anhydrous 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 anhydrous 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-9c52466517794e8791f0c1e06891e972
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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