Hydrogen Peroxide → 5-(3-Fluoro-benzyloxy)-pyridine-2-carboxylic acid

HRID 433214Notes

Reaction equation

HRID 433214 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]=[O:14])=[N:11][CH:12]=1.[OH:18]O>O=[Mn]=O.CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([OH:18])=[O:14])=[N:11][CH:12]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 111722915-(3-Fluoro-benzyloxy)-pyridine-2-carbaldehyde

Product 1

HCID 117367355-(3-Fluoro-benzyloxy)-pyridine-2-carboxylic acidYield 98%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of 5-(3-fluoro-benzyloxy)-pyridine-2-carbaldehyde (600 mg, 2.6 mmol), hydrogen peroxide (aq. 35%, 4 ml, 118 mmol) acetone (20 ml) and a catalytic amount of MnO2 was heated under reflux for 4 h. The solvent was evaporated and the residue was triturated with water. The precipitate was collected to give the title compound as a white solid (628 mg, 98%). MS: m/e =247.1 (M+).

Workup

  1. temperatureunder reflux for 4 h
  2. customThe solvent was evaporated
  3. customthe residue was triturated with water
  4. customThe precipitate was collected

Sources & evidence

ORD record
ord-afda2ff18a194016b0f3fb24722d91f6
Source dataset
uspto-grants-2003_12
Patent number
US06667327B2

Reaction notes

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