Sulfuric Acid → Methyl 4-fluoro-3-methoxybenzoate

HRID 71193Notes

Reaction equation

HRID 71193 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].S(=O)(=O)(O)O.[C:18](=O)([O-])O.[Na+]>CO>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:18])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 5984364-Fluoro-3-methoxybenzoic acid

Product 1

HCID 592847Methyl 4-fluoro-3-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-fluoro-3-methoxybenzoic acid (2.33 g) and sulfuric acid (0.2 mL) in methanol (20 mL) was heated under reflux for 10 hr, and allowed to cool to room temperature. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, the solvent was evaporated under reduced pressure, and water was added to the residue. The resultant precipitate was collected by filtration to give the title compound (2.31 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hr
  3. customthe solvent was evaporated under reduced pressure, and water
  4. additionwas added to the residue
  5. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-e0698cf517924db49b93a7991e44b852
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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