Ethanol → Ethyl 3-hydroxypicolinate

HRID 1984285Notes

Reaction equation

HRID 1984285 reaction equation
[OH:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:11](O)[CH3:12].S(=O)(=O)(O)O>C1C=CC=CC=1>[OH:1][C:2]1[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 134013-Hydroxypicolinic Acid

Product 1

HCID 15080989Ethyl 3-hydroxypicolinate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-Hydroxy-picolinic acid (15.6 g, 42.1 mmol), ethanol (360 mL), benzene (100 mL) and 98% sulfuric acid (6 mL) were heated under reflux for 40 h. After evaporation of the ethanol and benzene, the residue was dissolved in water, neutralized with sodium bicarbonate, and extracted with chloroform. The organic layer was dried (MgSO4), filtered, and then the solvent was evaporated to give ethyl 3-hydroxy-picolinate as a brown oily residue (11.0 g).

Workup

  1. temperatureunder reflux for 40 h
  2. customAfter evaporation of the ethanol and benzene
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with chloroform
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c6f880454e7745f09d0b6b5d60b96345
Source dataset
uspto-grants-2009_06
Patent number
US07544693B2

Reaction notes

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