Ethylene Glycol → 2-Pyridinyl-1,3-dioxolane

HRID 742474Notes

Reaction equation

HRID 742474 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[O:8].[CH2:9](O)[CH2:10][OH:11].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[O:8]1[CH2:9][CH2:10][O:11][CH:7]1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 142732-Pyridinecarboxaldehyde

Product 1

HCID 797732-Pyridinyl-1,3-dioxolaneYield 29.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-pyridinecarboxaldehyde (267 g, 2.5 mol), ethylene glycol (310.35 g, 5 mol), and 118.8 g (0.62 mol) of p-toluenesulfonic acid in 1.5 L of toluene placed in a 3 L flask fitted with a Dean Stark trap was allowed to reflux until the removal of water was complete. The mixture was concentrated in vacuo and the residue was poured into 800 mL of ice/10% potassium carbonate solution. The above mixture was extracted with ether (2×500 mL), and the organic layer was dried over sodium sulfate, filtered through an active charcoal/supercel and concentrated in vacuo to yield an oil. The oil was distilled (0.15 mm/90° C.) to afford 109.7 g (29.3%) of 2-(1,3-dioxolan-2-yl)-pyridine, as a pale yellow liquid.

Workup

  1. customplaced in a 3 L flask
  2. customfitted with a Dean Stark trap
  3. concentrationThe mixture was concentrated in vacuo
  4. additionthe residue was poured into 800 mL of ice/10% potassium carbonate solution
  5. extractionThe above mixture was extracted with ether (2×500 mL)
  6. dry with materialthe organic layer was dried over sodium sulfate
  7. filtrationfiltered through an active charcoal/supercel
  8. concentrationconcentrated in vacuo
  9. customto yield an oil
  10. distillationThe oil was distilled (0.15 mm/90° C.)

Sources & evidence

ORD record
ord-17f426d04fcc4227a096c71d0234f63a
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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