Ethylene Glycol → 2-Bromo-4-(1,3-dioxolan-2-yl)pyridine

HRID 1165759Notes

Reaction equation

HRID 1165759 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][N:3]=1.[CH2:10](O)[CH2:11][OH:12].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1C=CC=CC=1.O>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 27629912-Bromo-4-pyridinecarboxaldehyde

Product 1

HCID 146965072-Bromo-4-(1,3-dioxolan-2-yl)pyridineYield 82%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

60 g of 2-bromo-4-pyridinecarboxaldehyde was dissolved in 600 ml of benzene, and 40 g of ethylene glycol and 6 g of p-toluenesulfonic acid were put in the solution. The mixture was heated under reflux for 18 hours while water was removed by using a Dean-Stark trap. After the reaction, the reaction mixture was made basic by adding ice and a saturated aqueous solution of sodium hydrogen carbonate. The organic layer was washed with water and dried. The solvent was evaporated. The residue was distilled to give 60 g (yield 82%) of 2-bromo-4-(1,3-dioxolan-2-yl)pyridine.

Workup

  1. temperatureThe mixture was heated
  2. customwas removed
  3. customAfter the reaction
  4. additionby adding ice
  5. washThe organic layer was washed with water
  6. customdried
  7. customThe solvent was evaporated
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-c57f0961aa524ed79e3d2e0941c27b1d
Source dataset
uspto-grants-1990_03
Patent number
US04912101

Reaction notes

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