Sodium Hydroxide → 2-Fluoro-3,5-dimethoxybenzoic acid

HRID 459946Notes

Reaction equation

HRID 459946 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([O:12][CH3:13])[C:5]=1[F:14].[OH-].[Na+]>C(O)C>[F:14][C:5]1[C:6]([O:12][CH3:13])=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:4]=1[C:3]([OH:15])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59486234Methyl 2-fluoro-3,5-dimethoxybenzoate

Product 1

HCID 184447552-Fluoro-3,5-dimethoxybenzoic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 66.7 g (0.27 mol) of 2-fluoro-3,5-dimethoxy-benzoic acid methyl ester and 27 g (0.675 mol) of solid sodium hydroxide in 815 mL of anhydrous ethanol was refluxed for 24 hours. The ethanol was concentrated in vacuo and the solid residue was dissolved in water and extracted two times with ethyl ether. The aqueous layer was acidified with concentrated hydrochloric acid and a white precipitate was filtered, washed with cold water and dried in vacuo to afford 53.9 g (86.5%) of the title compound. MS (APCI) (m+1)/z 201.0.

Workup

  1. temperaturewas refluxed for 24 hours
  2. concentrationThe ethanol was concentrated in vacuo
  3. dissolutionthe solid residue was dissolved in water
  4. extractionextracted two times with ethyl ether
  5. filtrationa white precipitate was filtered
  6. washwashed with cold water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-0190bde5b1a546e2a6a3275b461d2221
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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