Methyl 3-fluoro-4-methoxybenzoate → 3-Fluoro-4-methoxybenzoic acid

HRID 906069Notes

Reaction equation

HRID 906069 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7]C)=[O:6]>[OH-].[K+].CO>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([OH:7])=[O:6]

Participants

3

Reactant 1

HCID 592848Methyl 3-fluoro-4-methoxybenzoate

Product 1

HCID 27334013-Fluoro-4-methoxybenzoic acidYield 83%

Reagents, catalysts & solvents 1

HCID 23689386Potassium hydroxide methanolSolvent

Procedure

A solution of methyl 3-fluoro-4-(methyloxy)benzoate (534 mg, 2.9 mmol) in 35% aqueous potassium hydroxide:methanol (1:4, 10 mL) was stirred at reflux for 1 hour. The solution was cooled to room temperature and the methanol was evaporated. The pH of the aqueous portion was brought to 2 using concentrated hydrochloric acid. The precipitate which formed was collected by filtration and washed with water to afford 400 mg, 2.4 mmol (83%) of 3-fluoro-4-methoxybenzoic acid. MS (EI) for C8H7FO3: 169 (M−H).

Workup

  1. temperatureat reflux for 1 hour
  2. customthe methanol was evaporated
  3. customThe precipitate which formed
  4. filtrationwas collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-df24ae92dbf94f7bb1e033a98cbadf5d
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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