Methyl 4-(pyridin-2-YL)benzoate → 4-(2-Pyridyl)Benzoic Acid

HRID 380231Notes

Reaction equation

HRID 380231 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:6][CH:5]=1>CO.[OH-].[Na+]>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:16])=[O:2])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 3358924Methyl 4-(pyridin-2-YL)benzoate

Product 1

HCID 8216924-(2-Pyridyl)Benzoic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

12.85 g (60.2 mmol) of 4-(pyridin-2-yl)-benzoic acid methyl ester in 125 ml of methanol and 67 ml of 1N sodium hydroxide solution are stirred at room temperature for 6 hours. The resulting solution is partially concentrated by evaporation; the aqueous residue is extracted with ethyl acetate and acidified to pH≈1.5 with 2N HCl solution. The title compound precipitates out and can be filtered off and washed with water: TLC (ethyl acetate): Rf=0.35; FAB MS (M+H)+=200.

Workup

  1. concentrationThe resulting solution is partially concentrated by evaporation
  2. extractionthe aqueous residue is extracted with ethyl acetate
  3. customThe title compound precipitates out and
  4. filtrationcan be filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-339b04d6120744378858aae7eaf5b5e0
Source dataset
uspto-grants-2001_10
Patent number
US06300519B1

Reaction notes

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