Potassium Hydroxide → 3-Benzyloxy-4-methoxypicolinic acid

HRID 350650Notes

Reaction equation

HRID 350650 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:17][OH:18])=[N:11][CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[Mn]([O-])(=O)(=O)=[O:22].[K+]>O>[CH2:1]([O:8][C:9]1[C:10]([C:17]([OH:22])=[O:18])=[N:11][CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 516875Potassium PermanganateHCID 199603213-Benzyloxy-2-hydroxymethyl-4-methoxypyridine

Product 1

HCID 199602893-Benzyloxy-4-methoxypicolinic acidYield 83.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Benzyloxy-2-hydroxymethyl-4-methoxypyridine (7.1 g) and 2.5 g of potassium hydroxide were suspended in 100 ml of water. While heating the suspension in a water bath, potassium permanganate (7.3 g) was added thereto, and the mixture was stirred. The precipitate was filtered, and was washed with 100 ml of methanol. The filtrate and the washings were combined, followed by concentration under the reduced pressure. The concentrate was adjusted to pH 1 by the addition of concentrated hydrochloric acid. The precipitate was filtered, washed with water, and then dried to give 6.3 g (yield 83.9%) of the title compound as colorless powder.

Workup

  1. temperatureWhile heating the suspension in a water bath
  2. filtrationThe precipitate was filtered
  3. washwas washed with 100 ml of methanol
  4. concentrationfollowed by concentration under the reduced pressure
  5. additionThe concentrate was adjusted to pH 1 by the addition of concentrated hydrochloric acid
  6. filtrationThe precipitate was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-7918c38eb2264104b46a1d5deb080734
Source dataset
uspto-grants-2007_02
Patent number
US07183278B1

Reaction notes

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