Reaction #42012

Reaction equation

Hydrogen peroxide

cis-cyclooctene

→

9-oxabicyclo[6.1.0] nonane

Yield 65.0%

Solvents

tert-butanol

Conditions

Workup

1. 1
   FiltrationThe catalyst was filtered off
2. 2
   Washwashed well with ether (80 ml)
3. 3
   WashThe combined organic layers were washed well with water (2×40 ml)
4. 4
   Dryingdried over magnesium sulphate
5. 5
   FiltrationAfter filtration the solvent
6. 6
   Otherwas removed under reduced pressure—20° C. at 50 mm of Hg—

Procedure

Hydrogen peroxide (30%, 2 ml) was added to a mixture of the catalyst from Example 48 (0.04 g) and cis-cyclooctene (1.4 g, 11.5 mmol) in tert-butanol (10 ml) at 30° C. under an atmosphere of nitrogen. The reaction mixture was stirred at 30° C. for 48 h under nitrogen. The catalyst was filtered off and washed well with ether (80 ml). The combined organic layers were washed well with water (2×40 ml) and then dried over magnesium sulphate. After filtration the solvent was removed under reduced pressure—20° C. at 50 mm of Hg—to afford 9-oxabicyclo[6.1.0] nonane as a white solid (0.95 g, 65%). M.p. 51° C., lit. m.p. 53-56° C.

Source