Ethylene Glycol → HCID 567357, compound

HRID 365159Notes

Reaction equation

HRID 365159 reaction equation
[CH:1]12[CH2:8][C:7](=[O:9])[CH:6]1[CH2:5][CH2:4][CH:3]=[CH:2]2.[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:9]1[CH2:10][CH2:11][O:12][C:7]21[CH2:8][CH:1]1[CH:6]2[CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 12507350HCID 12507350, compound

Product 1

HCID 567357HCID 567357, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 6.4 g bicyclo[4.2.0]oct-2-en-7-one (III), (Tetrahedron, 27, 615 (1971)), 18.62 g ethylene glycol, 100 ml benzene, and 25 mg p-toluenesulfonic acid is heated at reflux for 4 hr using a Dean-Stark trap to effect continuous removal of water. The cooled reaction mixture is poured onto 100 ml saturated sodium bicarbonate solution and the resulting mixture is extracted with three 75 ml portions of diethyl ether. The combined organic extract is washed with 100 ml saturated sodium chloride solution and is then dried over sodium sulfate. The solvent is removed under vacuum and the residue is distilled under vacuum to give 7.12 g of spiro[bicyclo[4.2.0]oct-2-ene-7,2'-[1.3]dioxolan] (IV).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 4 hr
  3. customremoval of water
  4. customThe cooled reaction mixture
  5. extractionthe resulting mixture is extracted with three 75 ml portions of diethyl ether
  6. extractionThe combined organic extract
  7. washis washed with 100 ml saturated sodium chloride solution
  8. dry with materialis then dried over sodium sulfate
  9. customThe solvent is removed under vacuum
  10. distillationthe residue is distilled under vacuum

Sources & evidence

ORD record
ord-380d3a32eb73444c88dea446be994508
Source dataset
uspto-grants-1986_08
Patent number
US04608388

Reaction notes

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