Picolyl chloride hydrochloride → HCID 12317325, compound

HRID 1605682Notes

Reaction equation

HRID 1605682 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[O-:10][CH2:11][CH3:12].[Na+]>CO>[CH2:11]([O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:12]

Participants

4

Reactant 2

HCID 23392Picolyl chloride hydrochlorideHCID 2723922Sodium ethoxide

Product 1

HCID 12317325HCID 12317325, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(Chloromethyl)pyridine hydrochloride (16.3 g., 0.1 mole) is dissolved in 100 ml. of methanol. Sodium ethoxide (0.22 mole of sodium dissolved in 150 ml. of ethanol) is added dropwise. The resulting mixture is heated at reflux for 18 hours, then filtered. The filtrate is concentrated. Water and ether are added, the aqueous phase is extracted with ether and the combined ethereal phases are washed with water and saturated aqueous sodium chloride, then dried over magnesium sulfate, concentrated and distilled to give 2-(ethoxymethyl)pyridine.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 18 hours
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated
  5. additionWater and ether are added
  6. extractionthe aqueous phase is extracted with ether
  7. washthe combined ethereal phases are washed with water and saturated aqueous sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. distillationdistilled

Sources & evidence

ORD record
ord-394e0e7e078e4cb8b8ad733de92fdcf6
Source dataset
uspto-grants-1976_04
Patent number
US03950522

Reaction notes

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