Ethylene Glycol → HCID 21936007, compound

HRID 279622Notes

Reaction equation

HRID 279622 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH2:8]([OH:11])[CH2:9]O.[OH-:12].[Na+].[CH3:14]S(C)=O>>[OH:12][CH2:14][CH2:9][CH2:8][O:11][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 679Dimethyl SulfoxideHCID 122884-ChloropyridineHCID 14798Sodium Hydroxide

Product 1

HCID 21936007HCID 21936007, compoundYield 45%

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloropyridine (7 g, 47 mmol), ethylene glycol (17.9 g, 235 mmol) and sodium hydroxide (4.67 g, 195 mmol) in DMSO (80 ml) was heated at 100° C. for 24 hours. Most of the solvent was removed by evaporation and the residue was diluted with ice water. The aqueous mixture was extracted with ethyl acetate, the extracts combined, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol mixtures (100/0 increasing to 97/3) to give 4-(3-hydroxypropoxy)pyridine (3.2 g, 45%).

Workup

  1. customMost of the solvent was removed by evaporation
  2. additionthe residue was diluted with ice water
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with methylene chloride/methanol mixtures (100/0 increasing to 97/3)

Sources & evidence

ORD record
ord-9f92ccacf23e44ef80bb45f4bdb1debb
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

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