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

HRID 880257Notes

Reaction equation

HRID 880257 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-c120e66446ae4db2b0a368a2f0f59095
Source dataset
uspto-grants-2015_03
Patent number
US08993555B2

Reaction notes

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