Methanol → Methyl 4,5-difluoro-2-hydroxybenzoate

HRID 1019835Notes

Reaction equation

HRID 1019835 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:12])[CH:3]=1.OS(O)(=O)=O.[CH3:18]O>>[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([O:8][CH3:18])=[O:7])=[C:4]([OH:12])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 120408324,5-Difluoro-2-hydroxybenzoic acid

Product 1

HCID 46311131Methyl 4,5-difluoro-2-hydroxybenzoateYield 74%

Procedure

A mixture of 4,5-difluoro-2-hydroxybenzoic acid (20 mmol), methanol (100 ml) and concentrated H2SO4 (5 ml) was refluxed for 48 h. Then, the reaction mixture was concentrated. The residue was dissolved in ethyl acetate, washed with brine and a saturated NaHCO3 solution and neutralized with citric acid. The organic layer was dried over MgSO4 and concentrated in vacuo to give the product. Yield: 2.8 g (97% purity, 74% yield).

Workup

  1. temperaturewas refluxed for 48 h
  2. concentrationThen, the reaction mixture was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give the product

Sources & evidence

ORD record
ord-a95824d141a64b4eb3367fc72a420a56
Source dataset
uspto-grants-2014_05
Patent number
US08716293B2

Reaction notes

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