Ethanol → Ethyl 6-chloropicolinate

HRID 706531Notes

Reaction equation

HRID 706531 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH2:11](O)[CH3:12].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 208126-Chloropicolinic acid

Product 1

HCID 11063114Ethyl 6-chloropicolinateYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A flask equipped with a condenser was charged with 6-chloropicolinic acid (23.5 g, 149 mmol), 100 mL of ethanol and 400 mL of toluene. To this was added 4 mL of sulfuric acid and the mixture was warmed to reflux for three hours, and then allowed to cool to ambient temperature. The reaction mixture was concentrated under reduced pressure and the resulting oil was taken up in 200 mL of ethyl acetate, washed with 10% aqueous potassium carbonate, dried over sodium sulfate and concentrated under reduced pressure to give 26 g of ethyl 6-chloropicolinate (94%).

Workup

  1. customA flask equipped with a condenser
  2. temperaturethe mixture was warmed
  3. temperatureto reflux for three hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. washwashed with 10% aqueous potassium carbonate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6635e9eee9c146d4b335a35245fa41c7
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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