Sodium Hydroxide → 3-(Pyridin-4-yl)benzoic acid

HRID 2202000Notes

Reaction equation

HRID 2202000 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([O:12]C)=[O:11])=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([OH:12])=[O:11])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 5152687Methyl 3-(4-pyridyl)benzoate

Product 1

HCID 27955623-(Pyridin-4-yl)benzoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(pyridin-4-yl)benzoate (450 mg, 2.1 mmol) in MeOH (5 mL) was added an aqueous solution of NaOH (1.5 mL, 0.4M). The mixture was stirred at room temperature for 2 h. The reaction solution was then concentrated, the residue was next dissolved in water and adjusted pH to 5-6 with the 2N HCl. After extraction with EtOAc, the organic layers were dried and concentrated to give the product desired (600 mg, Yield 90%). LCMS (m/z): 200.1 (M+1).

Workup

  1. concentrationThe reaction solution was then concentrated
  2. dissolutionthe residue was next dissolved in water
  3. extractionAfter extraction with EtOAc
  4. customthe organic layers were dried
  5. concentrationconcentrated
  6. customto give the product

Sources & evidence

ORD record
ord-dc825d82e0e04b26b6fbb722fa50f605
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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