Ethylene Glycol → HCID 58694829, compound

HRID 271303Notes

Reaction equation

HRID 271303 reaction equation
[CH:1]12[C:9](=[O:10])[CH:6]([CH2:7][CH2:8]1)[CH2:5][CH:4]=[CH:3][CH2:2]2.[CH2:11](O)[CH2:12][OH:13]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:10]1[CH2:11][CH2:12][O:13][C:9]21[CH:6]1[CH2:7][CH2:8][CH:1]2[CH2:2][CH:3]=[CH:4][CH2:5]1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 12556681Bicyclo[4.2.1]non-3-en-9-one

Product 1

HCID 58694829HCID 58694829, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of bicyclo[4.2.1]non-3-en-9-one (10 g, 73 mmol), ethyleneglycol (12.3 ml, 220 mmol) and p-toluenesulphonic acid monohydrate (100 mg) in toluene (250 ml) was refluxed in a Dean-Stark apparatus for four hours. The reaction mixture was cooled to ambient temperature and sequentially washed with water (3×50 ml) and brine (100 ml). The organic extract was dried over MgSO4 and concentrated in vacuo, to afford spiro[bicyclo[4.2.1]non-3-ene-9,2′-[1,3]dioxolane] (13.12 g, 99.5%).

Workup

  1. temperaturewas refluxed in a Dean-Stark apparatus for four hours
  2. washsequentially washed with water (3×50 ml) and brine (100 ml)
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-84b7c1c1bcb34cf9a138aa33cbc1680f
Source dataset
uspto-grants-2008_11
Patent number
US07452899B2

Reaction notes

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