Sodium Hydroxide → 3-(Pyridin-2-yl)benzoic acid

HRID 1507036Notes

Reaction equation

HRID 1507036 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([O:12]C)=[O:11].[OH-].[Na+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 3364101Methyl 3-(pyridin-2-yl)benzoate

Product 1

HCID 51525923-(Pyridin-2-yl)benzoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(pyridin-2-yl)benzoate (400 mg, 1.88 mmol) in MeOH (3 mL) was added aqueous of NaOH (1 mL, 40 mol %). The reaction mixture was stirred at room temperature for 3 h and concentrated. The crude residue was dissolved in water and the pH was adjusted to 5˜6 with 2N of HCl. The solution was extracted with ethyl acetate, brine, dried over sodium sulfate, filtered and concentrated. (350 mg, yield 93%) MS (ESI+) e/z: 200.1 [M+1]+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe crude residue was dissolved in water
  3. extractionThe solution was extracted with ethyl acetate, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a89da6cea659468590adb1164a31b108
Source dataset
uspto-grants-2015_12
Patent number
US09221794B2

Reaction notes

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