Lithium hydroxide, monohydrate → 4-[6-(Trifluoromethyl)pyridin-3-yl]benzoic acid

HRID 1867787Notes

Reaction equation

HRID 1867787 reaction equation
C[O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:15]=2)=[CH:6][CH:5]=1.O.[OH-].[Li+]>O1CCCC1.O>[F:18][C:16]([F:17])([F:19])[C:13]1[N:12]=[CH:11][C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:20])=[O:2])=[CH:5][CH:6]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67370143HCID 67370143, compound

Product 1

HCID 231205374-[6-(Trifluoromethyl)pyridin-3-yl]benzoic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Procedure G′: 4-(6-Trifluoromethyl-pyridin-3-yl)-benzoic acid methyl ester (0.57 g, 2 mmol) is dissolved in tetrahydrofuran/water (9:1)(25 ml), lithium hydroxide monohydrate (0.9 g, 2.2 mmol) is added and the mixture is heated under reflux overnight. The mixture is concentrated under reduced pressure and partitioned between water and ethyl acetate. The aqueous layer is acidified and the resulting precipitate is collected by filtration to give the 4-(6-trifluoromethyl-pyridin-3-yl)-benzoic acid. MS (FIA)267 (MH−)

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. concentrationThe mixture is concentrated under reduced pressure
  4. custompartitioned between water and ethyl acetate
  5. filtrationthe resulting precipitate is collected by filtration

Sources & evidence

ORD record
ord-15bbde3bd8944176803228a38af867dc
Source dataset
uspto-grants-2009_12
Patent number
US07632857B2

Reaction notes

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