Potassium Permanganate → 5-(3-Chloro-benzyloxy)-2-pyridinecarboxylic acid

HRID 1395186Notes

Reaction equation

HRID 1395186 reaction equation
[Cl: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]([CH2:13][OH:14])=[N:11][CH:12]=1.[Mn]([O-])(=O)(=O)=[O:19].[K+]>O>[Cl: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:19])=[O:14])=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 234671675-(m-Chlorobenzyloxy)-2-pyridinemethanol

Product 1

HCID 234671725-(3-Chloro-benzyloxy)-2-pyridinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 13.1 g of 5-(m-chloro-benzyloxy)-2-pyridinemethanol and 250 ml of water is stirred vigorously at 25°. To this mixture is added 11.5 g of potassium permanganate in several portions. Then the mixture is filtered, the precipitated manganese dioxide washed with hot water, the washing is combined with the filtrate, concentrated to a small volume and then acidified with aqueous hydrochloric acid. The precipitated product is collected and recrystallized from ethyl acetate to yield 5-(3-chloro-benzyloxy)-2-pyridinecarboxylic acid melting at 176°-177°.

Workup

  1. filtrationThen the mixture is filtered
  2. washthe precipitated manganese dioxide washed with hot water
  3. concentrationconcentrated to a small volume
  4. customThe precipitated product is collected
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6d8dadf283284758ae4da04fddabd450
Source dataset
uspto-grants-1980_05
Patent number
US04202901

Reaction notes

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