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

HRID 1458483Notes

Reaction equation

HRID 1458483 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-c5e849a0aa0342aba677fc63f14405bd
Source dataset
uspto-grants-1998_12
Patent number
US05849911

Reaction notes

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