Ethylene Glycol → 1-(2-Chloro-4-pyridyl)-1-ethylenedioxyethane

HRID 1155534Notes

Reaction equation

HRID 1155534 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:22](O)[CH2:23][OH:24]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]2[O:10][CH2:22][CH2:23][O:24][CH2:9]2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 131452551-(2-Chloropyridin-4-yl)ethan-1-one

Product 1

HCID 867381251-(2-Chloro-4-pyridyl)-1-ethylenedioxyethane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 21.3 g. (0.137 mole) of 1-(2-chloro-4-pyridyl)ethanone and 0.5 g. of p-toluenesulfonic acid in 40 ml. of ethylene glycol and 300 ml. of toluene was placed in a flask fitted with a Dean-Stark trap and condenser, and was heated at reflux temperature for 16 hours. The mixture was cooled and concentrated in vacuo to give an oil which was purified by distillation under reduced pressure, 23.6 g. (86%), b.p. 65° C. (0.05 torr).

Workup

  1. additionA mixture of 21.3 g
  2. customfitted with a Dean-Stark trap and condenser
  3. temperaturewas heated
  4. temperatureat reflux temperature for 16 hours
  5. temperatureThe mixture was cooled
  6. concentrationconcentrated in vacuo
  7. customto give an oil which
  8. distillationwas purified by distillation under reduced pressure, 23.6 g

Sources & evidence

ORD record
ord-52e00f3349c649d0b14d8190b2478323
Source dataset
uspto-grants-1981_11
Patent number
US04302464

Reaction notes

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