Potassium Carbonate → (2-Chloropyridin-4-yl)methanol

HRID 907554Notes

Reaction equation

HRID 907554 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([Cl:9])[CH:4]=1.C(=O)([O-])[O-:11].[K+].[K+]>O>[Cl:9][C:5]1[CH:4]=[C:3]([CH2:2][OH:11])[CH:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 111265732-Chloro-4-(chloromethyl)pyridine

Product 1

HCID 7062237(2-Chloropyridin-4-yl)methanolYield 9.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The crude product of 4-(chloromethyl)-2-chloropyridine (9.25 g), and potassium carbonate (9.5 g, 68.7 mmol) were suspended in water (100 mL) and heated at reflux for 2.5 h. The mixture was allowed to cool to room temperature and the phases were separated. The oily phase was further extracted with water. The combined aqueous phases were washed with hexanes and extracted with EtOAc. The combined EtOAc phases were dried over MgSO4 and concentrated in vacuo to yield 2-Chloro-4-pyridinemethanol as an off white solid (762 mg, 9.3% yield over 2 steps).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2.5 h
  3. customthe phases were separated
  4. extractionThe oily phase was further extracted with water
  5. washThe combined aqueous phases were washed with hexanes
  6. extractionextracted with EtOAc
  7. dry with materialThe combined EtOAc phases were dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4b9b158f89cf4c01802d9784d95fcf8a
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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