Ethylene Glycol → 3-(2-Methyl-1,3-dioxolan-2-yl)pyridine

HRID 1029617Notes

Reaction equation

HRID 1029617 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[CH2:10](O)[CH2:11][OH:12].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:2][C:1]1([C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)[O:12][CH2:11][CH2:10][O:3]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 95893-Acetylpyridine

Product 1

HCID 2807153-(2-Methyl-1,3-dioxolan-2-yl)pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Acetylpyridine (10 g), ethylene glycol (50 ml) and p-toluenesulfonic acid (0.5 g) were dissolved in toluene and the solution was refluxed at 150° C. for 1 day with the by-product water being constantly removed. After cooling, saturated aqueous sodium hydrogen carbonate and toluene were added and the mixture was stirred and allowed to stand. The aqueous layer was separated and extracted with 2 portions of toluene. The toluene layers were combined, washed sequentially with saturated aqueous sodium hydrogen carbonate, water and aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. Finally the solvent was distilled off under reduced pressure to give 2-methyl-2-(pyridin-3-yl)-1,3-dioxolane (13.6 g).

Workup

  1. customconstantly removed
  2. temperatureAfter cooling
  3. additionsaturated aqueous sodium hydrogen carbonate and toluene were added
  4. customThe aqueous layer was separated
  5. extractionextracted with 2 portions of toluene
  6. washwashed sequentially with saturated aqueous sodium hydrogen carbonate, water and aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationFinally the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b75e6f7685244bc287fe166ff305ece1
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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