Picolyl chloride hydrochloride → 2-(Methoxymethyl)pyridine

HRID 1076366Notes

Reaction equation

HRID 1076366 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[CH3:10][O-:11].[Na+]>CO>[CH3:10][O:11][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 23392Picolyl chloride hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 2532202-(Methoxymethyl)pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(Chloromethyl)pyridine hydrochloride (16.3 g., 0.1 mole) is dissolved in 100 ml. of methanol. Freshly prepared sodium methoxide (5 g., 0.22 mole of sodium dissolved in 150 ml. of methanol) 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-(methoxymethyl)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-1d48ab535ad4491d97f358a9c06b451c
Source dataset
uspto-grants-1976_05
Patent number
US03956494

Reaction notes

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