Ethylene Glycol → HCID 15166210, compound

HRID 727886Notes

Reaction equation

HRID 727886 reaction equation
[Na].Cl[C:3]1[CH:8]=[CH:7][N+:6]([O-:9])=[C:5]([CH3:10])[C:4]=1[CH3:11].[CH2:12]([OH:15])[CH2:13][OH:14]>>[OH:14][CH2:13][CH2:12][O:15][C:3]1[CH:8]=[CH:7][N+:6]([O-:9])=[C:5]([CH3:10])[C:4]=1[CH3:11]

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 5360545SodiumHCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-ium

Product 1

HCID 15166210HCID 15166210, compound

Conditions

Temperature
100 °C

Procedure

4.60 g (0.2 mol) of metallic sodium was dissolved in 80 ml of ethylene glycol under cooling with ice to obtain a solution. This solution was stirred in a nitrogen atmosphere at 100° C. for one hour, followed by the addition of 15.76 g (0.1 mol) of 4-chloro-2,3-dimethylpyridine N-oxide at a room temperature. The obtained mixture was stirred at 120° C. for 2 hours. After the completion of the reaction, the reaction mixture was distilled to dryness to remove the ethylene glycol. The obtained residue was purified by silica gel column chromatography (solvent: chloroform/methanol=19:1) to obtain 13.28 g of 4-(2-hydroxyethoxy)-2,3-dimethylpyridine N-oxide as a white crystal.

Workup

  1. temperatureunder cooling with ice
  2. customto obtain a solution
  3. stirringThe obtained mixture was stirred at 120° C. for 2 hours
  4. customAfter the completion of the reaction
  5. distillationthe reaction mixture was distilled to dryness
  6. customto remove the ethylene glycol
  7. customThe obtained residue was purified by silica gel column chromatography (solvent: chloroform/methanol=19:1)

Sources & evidence

ORD record
ord-4e3de836c5a34b4dac4dcbff718e4a27
Source dataset
uspto-grants-1991_09
Patent number
US05045552

Reaction notes

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