Reaction #74972

Reaction equation

1,2,3,4,9,9-hexachloro-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione

hydrogen peroxide

sodium carbonate

→

1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,4a,6,7,8a-hexahydro-1,4-methanonaphthalene-5,8-dione

Solvents

ethanol

Conditions

Workup

1. 1
   workup.ADDITIONwere added slowly to a solution of 200 ml
2. 2
   TemperatureThe solution was then cooled to 10°-13° C.
3. 3
   Othera white precipitate formed
4. 4
   FiltrationThis solid was filtered
5. 5
   Otherrecrystallized from ethanol, m.p. 180°-181° C.

Procedure

38 g. of 1,2,3,4,9,9-hexachloro-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione, prepared according to Example 1, were added slowly to a solution of 200 ml. of ethanol containing 20 ml. of 30% hydrogen peroxide and 13 g. of sodium carbonate at such a rate that the temperature was maintained at 40°-50° C. The yellow color of the dione disappeared quickly. The solution was then cooled to 10°-13° C. and a white precipitate formed. This solid was filtered and recrystallized from ethanol, m.p. 180°-181° C.

Source