Sodium Carbonate → 3-Fluoro-4-methoxybenzoic acid

HRID 626142Notes

Reaction equation

HRID 626142 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])C#N.[C:12](=[O:15])([O-])[O-:13].[Na+].[Na+]>O.S(=O)(=O)(O)O>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[C:12]([OH:13])=[O:15]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 27745483-Fluoro-4-methoxybenzonitrile

Product 1

HCID 27334013-Fluoro-4-methoxybenzoic acidYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

3-Fluoro-4-methoxybenzonitrile (2.0 g, 13.2 mmol) in water (5 mL) and concentrated sulphuric acid (5 mL) was heated at 110° C. for 4 hours. The solution was then cooled to room temperature and neutralized with solid sodium carbonate. Acidification with glacial acetic acid leads to a white precipitate, which was collected by filtration and dissolved in dichloromethane. The resulting solution was dried over sodium sulfate, filtered, and concentrated to give the product as a beige-colored solid (2.03 g, 90% yield).

Workup

  1. filtrationAcidification with glacial acetic acid leads to a white precipitate, which was collected by filtration
  2. dissolutiondissolved in dichloromethane
  3. dry with materialThe resulting solution was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-416c83e1f8b64d3bae9f7d5d523a75f9
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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