Sodium Hydroxide → 2,6-Difluoro-3,5-dimethoxybenzoic acid

HRID 459943Notes

Reaction equation

HRID 459943 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[C:9]([F:10])=[C:8]([O:11][CH3:12])[CH:7]=[C:6]([O:13][CH3:14])[C:5]=1[F:15].[OH-].[Na+]>C(O)C>[F:10][C:9]1[C:8]([O:11][CH3:12])=[CH:7][C:6]([O:13][CH3:14])=[C:5]([F:15])[C:4]=1[C:3]([OH:16])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59486229Methyl 2,6-difluoro-3,5-dimethoxybenzoate

Product 1

HCID 184447022,6-Difluoro-3,5-dimethoxybenzoic acidYield 82.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 115 g (0.49 mol) of 2,6-difluoro-3,5-dimethoxy benzoic acid methyl ester and 42.9 g (1.07 mol) of solid sodium hydroxide in 1.4 L 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 give 87.9 g (81%) of the title compound. MS (APCI) (m+1)/z 219.1.

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-f2d00457297a4452b22bed72baeea1e4
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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