Ethylene Glycol → HCID 22281024, compound

HRID 1058154Notes

Reaction equation

HRID 1058154 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[CH2:8][CH:9]=[O:10].[CH2:11](O)[CH2:12][OH:13].C1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[CH2:8][CH:9]1[O:13][CH2:12][CH2:11][O:10]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 1140TolueneHCID 55627480376-88-1

Product 1

HCID 22281024HCID 22281024, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

40.0 g of (5-norbornen-2-yl)acetoaldehyde, 23.0 g of ethylene glycol, 120 ml of toluene and 200 mg of p-toluenesulfonic acid were mixed and heated under reflux for one hour while the water formed was removed through an H tube. The reaction mixture was allowed to cool down and poured into 50 ml of saturated sodium bicarbonate water. The resulting mixture separated into two layers. The organic layer was washed with water and saturated sodium chloride water, dried over anhydrous sodium sulfate, and concentrated in vacuum. It was further purified by vacuum distillation, obtaining 50.3 g of 2-(5-norbornen-2-yl)methyl-1,3-dioxolane (boiling point 63° C./200 Pa, yield 95%).

Workup

  1. temperatureheated
  2. customformed
  3. customwas removed through an H tube
  4. temperatureto cool down
  5. additionpoured into 50 ml of saturated sodium bicarbonate water
  6. customThe resulting mixture separated into two layers
  7. washThe organic layer was washed with water and saturated sodium chloride water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuum
  10. distillationIt was further purified by vacuum distillation

Sources & evidence

ORD record
ord-4ee75d8673e74a8db963b4ae9bbba8cf
Source dataset
uspto-grants-2003_02
Patent number
US06515149B2

Reaction notes

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