Ethylene Glycol → Spiro[bicyclo[2.2.2]octane-2,2'-[1,3]dioxolane]-5-one

HRID 220230Notes

Reaction equation

HRID 220230 reaction equation
[CH:1]12[CH2:9][CH2:8][CH:4]([C:5](=[O:7])[CH2:6]1)[CH2:3][C:2]2=[O:10].[CH2:11](O)[CH2:12][OH:13].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:7]1[CH2:11][CH2:12][O:13][C:5]21[CH2:6][CH:1]1[CH2:9][CH2:8][CH:4]2[CH2:3][C:2]1=[O:10]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 13570060Bicyclo(2.2.2)octane-2,5-dione

Product 1

HCID 14789039Spiro[bicyclo[2.2.2]octane-2,2'-[1,3]dioxolane]-5-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 4.0 g of rac-(1R*,4R*)-bicyclo[2.2.2]octane-2,5-dione (intermediate K1A.1), dissolved in 120 mL of toluene, 1.7 mL of ethylene glycol and 0.27 g of TsOH were added and the solution was heated under vigorous stirring to reflux for 3.5 h. The reaction mixture was cooled to rt, quenched with saturated aq. NaHCO3, extracted with Et2O, and the organic phase was evaporated. The crude product was purified by CC with Hex-EtOAc (7:3) to yield 2.41 g of rac-(1R*,4R*)-spiro[bicyclo[2.2.2]octane-2,2′-[1,3]dioxolan]-5-one as yellow oil.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 3.5 h
  3. customquenched with saturated aq. NaHCO3
  4. extractionextracted with Et2O
  5. customthe organic phase was evaporated
  6. customThe crude product was purified by CC with Hex-EtOAc (7:3)

Sources & evidence

ORD record
ord-2dc0590e8f8a4ae99584465a45e4126e
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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