Ethanol → Ethyl 3-hydroxypicolinate

HRID 1017665Notes

Reaction equation

HRID 1017665 reaction equation
[OH:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.O.[CH2:17](O)[CH3:18]>C1C=CC=CC=1>[OH:1][C:2]1[C:3]([C:8]([O:10][CH2:17][CH3:18])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 134013-Hydroxypicolinic Acid

Product 1

HCID 15080989Ethyl 3-hydroxypicolinate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-Hydroxypicolinic acid (12.5 g, 900 mmol) was suspended in a mixture of ethanol (300 ml) and benzene (100 ml). Sulfuric acid (5 ml) was added and the reaction mixture was heated at reflux with azeotropic removal of water via Dean Stark trap. After the reaction was complete, the organics were removed in vacuo. The residue was dissolved in water, basified with sodium carbonate and extracted with ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate, concentrated in vacuo to give ethyl 3-hydroxypicolinate (15 g).

Workup

  1. temperaturethe reaction mixture was heated
  2. customthe organics were removed in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af4b55629ea24952bd6cd659275915a7
Source dataset
uspto-grants-2002_11
Patent number
US06479507B2

Reaction notes

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