Water → 2,6-Bis(trifluoromethyl)nicotinic acid

HRID 1253124Notes

Reaction equation

HRID 1253124 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[C:8]([C:9]([O:11]C)=[O:10])=[CH:7][CH:6]=[C:5]([C:13]([F:16])([F:15])[F:14])[N:4]=1.[OH-].[K+].O>C(O)C>[F:17][C:2]([F:1])([F:18])[C:3]1[C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=[C:5]([C:13]([F:16])([F:14])[F:15])[N:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 11507333Methyl 2,6-bis(trifluoromethyl)nicotinate

Product 1

HCID 141304952,6-Bis(trifluoromethyl)nicotinic acidYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7 g (0.026 mole) of the product of Example 7, 5 g of potassium hydroxide, 10 ml of H2O and 35 ml ethanol were stirred overnight at reflux. The solvent was then removed under vacuum. H2O was added to the residue. This aqueous layer was extracted 2X with ether (ether layer discarded). The aqueous layer was then acidified with conc. HCl. The product was extracted with ether. The ether layer was washed 2X with H2O and dried over MgSO4. The ether was then removed under vacuum and the resulting solid was dried to yield 6.07 g (91%) of a white solid. M.P. 102°-104° C.

Workup

  1. temperatureat reflux
  2. customThe solvent was then removed under vacuum
  3. additionH2O was added to the residue
  4. extractionThis aqueous layer was extracted 2X with ether (ether layer discarded)
  5. extractionThe product was extracted with ether
  6. washThe ether layer was washed 2X with H2O
  7. dry with materialdried over MgSO4
  8. customThe ether was then removed under vacuum
  9. customthe resulting solid was dried

Sources & evidence

ORD record
ord-2fb91d6f4e94499f82418df78cb1251a
Source dataset
uspto-grants-1988_05
Patent number
US04747871

Reaction notes

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