Ethylene Glycol → HCID 15166210, compound

HRID 357542Notes

Reaction equation

HRID 357542 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-ffcf7880c1514b269c31c681edcc07cc
Source dataset
uspto-grants-1998_11
Patent number
US05840910

Reaction notes

Loading…