Methanol → Methyl 3-fluoro-4-hydroxybenzoate

HRID 1695224Notes

Reaction equation

HRID 1695224 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([OH:11])=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1604563-Fluoro-4-hydroxybenzoic acid

Product 1

HCID 7019368Methyl 3-fluoro-4-hydroxybenzoateYield 85%

Procedure

3-Fluoro-4-hydroxy-benzoic acid (5 g, 32.0 mmol) was dissolved in MeOH (50 mL) and catalytic quantity of sulfuric acid (1 mL) was added. The mixture was refluxed overnight, after which the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated NaHCO3 to basic pH. The organic phase was dried and evaporated under reduced pressure, and the residue was used without further purification (yield 85%).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customafter which the solvent was evaporated under reduced pressure
  3. dissolutionthe crude was dissolved in DCM
  4. washwashed with saturated NaHCO3 to basic pH
  5. customThe organic phase was dried
  6. customevaporated under reduced pressure
  7. customthe residue was used without further purification (yield 85%)

Sources & evidence

ORD record
ord-11b842cd794f49e8b56703a346c739fa
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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