Lithium hydroxide, monohydrate → 2-(5-(Trifluoromethyl)pyridin-2-yl)benzoic acid

HRID 51912Notes

Reaction equation

HRID 51912 reaction equation
C([O:4][C:5](=[O:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=1)(C)C.O.[OH-].[Li+]>O1CCCC1CO.O>[F:20][C:18]([F:19])([F:21])[C:15]1[CH:16]=[CH:17][C:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5]([OH:22])=[O:4])=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 698912952-(5-Trifluoromethyl-pyridin-2-yl)-benzoic acid isopropyl ester

Product 1

HCID 227369092-(5-(Trifluoromethyl)pyridin-2-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 66577907Tetrahydrofuran-methanol waterSolvent

Procedure

2-(5-Trifluoromethyl-pyridin-2-yl)-benzoic acid isopropyl ester was dissolved in 10 ml of a 3:1:1 mixture of tetrahydrofuran-methanol-water, and lithium hydroxide monohydrate (161 mg, 3.84 mmol) was added. After stirring for 3 h at room temperature, the volatiles were removed under vacuum and 5 ml of water were added to the mixture, which was brought to pH 6 with 1N HCl. The resulting slurry was extracted with ethyl acetate, the combined organic layers were dried (magnesium sulfate), filtered and concentrated under vacuum to provide the title compound.

Workup

  1. additionwas added
  2. customthe volatiles were removed under vacuum and 5 ml of water
  3. additionwere added to the mixture, which
  4. extractionThe resulting slurry was extracted with ethyl acetate
  5. dry with materialthe combined organic layers were dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-15d651bafd9244f8b7ddf9e9319aa1c2
Source dataset
uspto-grants-2004_03
Patent number
US06713489B2

Reaction notes

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