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

HRID 1780890Notes

Reaction equation

HRID 1780890 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>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

5

Reactant 3

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

Product 1

HCID 797732-Pyridinyl-1,3-dioxolaneYield 82.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-pyridinecarboxaldehyde (300 g), 300 mL of ethylene glycol, 3 L of toluene and 100 g of p-toluenesulfonic acid in a 5 L 3 neck-flask equipped with a Dean-Stark head was refluxed for 4 h, separating the water formed. The mixture was concentrated in vacuo to 1/2 of its volume, and poured into a 5 L flask containing a cold (5° C.) sodium bicarbonate solution. The aqueous layer was extracted with methylene chloride (3×500 mL), the combined organic layer was dried over sodium sulfate, and concentrated in vacuo to yield a dark oil. The oil was distilled (1 mm/100°-110° C.) to afford 349.1 g (82.4%) of 2-(1,3-dioxolan-2-yl)pyridine.

Workup

  1. customequipped with a Dean-Stark head
  2. temperaturewas refluxed for 4 h
  3. customseparating the water
  4. customformed
  5. concentrationThe mixture was concentrated in vacuo to 1/2 of its volume
  6. additionpoured into a 5 L flask
  7. additioncontaining a cold (5° C.) sodium bicarbonate solution
  8. extractionThe aqueous layer was extracted with methylene chloride (3×500 mL)
  9. dry with materialthe combined organic layer was dried over sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customto yield a dark oil
  12. distillationThe oil was distilled (1 mm/100°-110° C.)

Sources & evidence

ORD record
ord-499e7dfea3e34cb2af71162c1e65aaea
Source dataset
uspto-grants-1997_05
Patent number
US05631264

Reaction notes

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