2-Methoxyethanol → HCID 20280058, compound

HRID 1247932Notes

Reaction equation

HRID 1247932 reaction equation
[Na].Cl.Cl[CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.[CH3:11][O:12][CH2:13][CH2:14][OH:15]>>[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 80192-Methoxyethanol2×HCID 745704-(Chloromethyl)pyridinium chlorideHCID 5360545Sodium

Product 1

HCID 20280058HCID 20280058, compound

Procedure

To a solution of sodium (7.57 g) in 2-methoxyethanol (135 ml) was added dropwise a solution of 4-chloromethylpyridine hydrochloride (22.5 g) in 2-methoxyethanol (150 ml) under cooling in an ice-salt bath and stirring. The mixture was stirred for 45 minutes at 65° C. and evaporated under reduced pressure. The residue was dissolved in water (500 ml) and the solution was extracted with chloroform. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated. The residual oil was distilled to give 4-(2-methoxyethoxymethyl)pyridine (21.56 g), bp 98° to 101° C. at 3 to 3.5 mmHg.

Workup

  1. temperatureunder cooling in an ice-salt bath
  2. stirringThe mixture was stirred for 45 minutes at 65° C.
  3. customevaporated under reduced pressure
  4. dissolutionThe residue was dissolved in water (500 ml)
  5. extractionthe solution was extracted with chloroform
  6. washThe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. distillationThe residual oil was distilled

Sources & evidence

ORD record
ord-0fb5cb7bddda45a4acc41ebc7736866c
Source dataset
uspto-grants-1985_06
Patent number
US04521413

Reaction notes

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