Potassium Permanganate → Picolinic acid, 5-(3-chloropropoxy)-

HRID 1395193Notes

Reaction equation

HRID 1395193 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][OH:13])=[N:10][CH:11]=1.[Mn]([O-])(=O)(=O)=[O:15].[K+]>O>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([OH:15])=[O:13])=[N:10][CH:11]=1

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 233352865-(3-Chloropropoxy)-2-pyridine methanol

Product 1

HCID 3055221Picolinic acid, 5-(3-chloropropoxy)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 30.0 g of 5-(3-chloropropoxy)-2-pyridine methanol and 1,200 ml of water is stirred vigorously at 5°. To this mixture is added 31.0 of potassium permanganate in several portions during which time the temperature of the mixture rises to 25° and then the mixture is stirred at 25° for 30 minutes. Then the mixture is filtered, the precipitated manganese dioxide washed with several portions of water, the washing is combined with the filtrate and the resulting aqueous solution is adjusted to pH 5. Then the aqueous solution is evaporated to a small volume and the concentrate is extracted several times with ethyl acetate. After the extracts are combined, the combined ethyl acetate solution is washed and dried. The solution is filtered and the filtrate evaporated to yield 5-(3-chloropropoxy)-2-pyridinecarboxylic acid melting at 120°-121°.

Workup

  1. customrises to 25°
  2. stirringthe mixture is stirred at 25° for 30 minutes
  3. filtrationThen the mixture is filtered
  4. washthe precipitated manganese dioxide washed with several portions of water
  5. customThen the aqueous solution is evaporated to a small volume
  6. extractionthe concentrate is extracted several times with ethyl acetate
  7. washthe combined ethyl acetate solution is washed
  8. customdried
  9. filtrationThe solution is filtered
  10. customthe filtrate evaporated

Sources & evidence

ORD record
ord-dc27a5140f5040a8bfe6d14aa146bd78
Source dataset
uspto-grants-1980_05
Patent number
US04202901

Reaction notes

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