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

HRID 742438Notes

Reaction equation

HRID 742438 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].O.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 142732-PyridinecarboxaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 797732-Pyridinyl-1,3-dioxolaneYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-pyridinecarboxaldehyde (500 g, 4.67 mol), 561 mL of ethylene glycol, and 234 g of p-toluenesulfonic acid monohydrate in 5.8 L of toluene was heated to reflux while distilling (azeotropic) water formed during the reaction. The solvent was removed in vacuo and the residue was distilled to afford 475 g (67%) of 2-(1,3-dioxolan-2-yl)pyridine (Formula V: R1 =H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. distillationwhile distilling (azeotropic) water
  4. customformed during the reaction
  5. customThe solvent was removed in vacuo
  6. distillationthe residue was distilled

Sources & evidence

ORD record
ord-4e760bafeccd4509b7101e1c9747c6d6
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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