Potassium Hydroxide → 3-(Hexyloxy)-2-pyridinecarboxylic acid

HRID 1587687Notes

Reaction equation

HRID 1587687 reaction equation
[CH2:1]([O:7][C:8]1[C:9]([C:14]([O:16]CCCCCC)=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[K+]>CO>[CH2:1]([O:7][C:8]1[C:9]([C:14]([OH:16])=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19756117HCID 19756117, compound

Product 1

HCID 197561453-(Hexyloxy)-2-pyridinecarboxylic acidYield 111.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 10 ml of methanol was dissolved 2.50 g (8.1 mmol) of hexyl 3-hexyloxypicolinate and 10 ml of a 10% potassium hydroxide solution was added thereto, followed by refluxing for 1.5 hours. The solvent was distilled off under a reduced pressure and the residue was dissolved in 30 ml of water and, after the pH of the solution was adjusted to about 2 with 6N hydrochloric acid, was extracted with dichloromethane. After drying over anhydrous sodium sulfate, the solvent was distilled off to obtain 2.01 g of an oily product. Since the recrystallization cannot be effected in any solvents, the washing with hexane was repeated to obtain 0.80 g of the oily product, which was directly used in the subsequent reaction.

Workup

  1. additionwas added
  2. temperatureby refluxing for 1.5 hours
  3. distillationThe solvent was distilled off under a reduced pressure
  4. dissolutionthe residue was dissolved in 30 ml of water
  5. extractionwas extracted with dichloromethane
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-8be43bf36a6144ed8bbc20675782e7de
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

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