Methanol → HCID 22999141, compound

HRID 1166717Notes

Reaction equation

HRID 1166717 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([OH:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:17]O>>[F:1][C:2]1[C:10]([F:11])=[C:9]([OH:12])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27793072,3-difluoro-4-hydroxybenzoic acid

Product 1

HCID 22999141HCID 22999141, compoundYield 62%

Procedure

To the 2,3-difluoro-4-hydroxybenzoic acid (800 mg, 5.1 mmol) dissolved in anhydrous methanol (50 mL) was added thionyl chloride (0.55 mL, 7.3 mmol). After stirring the solution at room temperature for 16 hours, the solvent was evaporated. The residue was taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate, water, brine, and dried over MgSO4 to give methyl 2,3-difluoro-4-hydroxybenzoate (540 mg, 62%).

Workup

  1. customthe solvent was evaporated
  2. washwashed with saturated aqueous sodium bicarbonate, water, brine
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-f28a623de5224e8d9d5d785a3b1133aa
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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