Ethylene Glycol → HCID 22281032, compound

HRID 1058156Notes

Reaction equation

HRID 1058156 reaction equation
[CH2:1]([O:3][CH:4]=[CH:5][CH2:6][CH2:7][CH:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH:10]=[CH:11]2)[CH3:2].C(O)C[OH:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH:9]12[CH2:14][CH:12]([CH:11]=[CH:10]1)[CH2:13][CH:8]2[CH2:7][CH2:6][CH2:5][CH:4]1[O:17][CH2:2][CH2:1][O:3]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 69733599HCID 69733599, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 22281032HCID 22281032, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Next, the thus obtained 5-(4-ethoxy-3-buten-1-yl)-2-norbornene was mixed with 90 g of ethylene glycol, 1.0 g of p-toluenesulfonic acid and 300 ml of toluene and heated under reflux for one hour. The reaction mixture was allowed to cool down and poured into 100 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 177 g of 2-{3-(5-norbornen-2-yl)-1-propyl}-1,3-dioxolane (boiling point 92° C./27 Pa, yield 85%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for one hour
  3. temperatureto cool down
  4. customThe resulting mixture separated into two layers
  5. washThe organic layer was washed with water and saturated sodium chloride water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuum
  8. distillationIt was further purified by vacuum distillation

Sources & evidence

ORD record
ord-6565c6debb194bdaaffe392505f666aa
Source dataset
uspto-grants-2003_02
Patent number
US06515149B2

Reaction notes

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