Reaction #74973

Reaction equation

methyl-p-benzoquinone

hexachlorocyclopentadiene

→

1,2,3,4,9,9-hexachloro-1,4,4a,8a-tetrahydro-6-methyl-1,4-methanonaphthalene-5,8-dione

Solvents

toluene

Conditions

Workup

1. 1
   workup.ADDITIONwas added 20 ml
2. 2
   TemperatureThis reaction mixture was then heated at 130°-140° C. for 3 hours
3. 3
   WashThis solid was washed with Skelly "B" solvent several times on a Buchner funnel
4. 4
   Otherrecrystallized from a Skelly "B"-benzene mixed solvent (20/80)
5. 5
   OtherPale yellow crystals were obtained

Procedure

To a mixture of methyl-p-benzoquinone (60 g.), and hexachlorocyclopentadiene (140 g.), was added 20 ml. of toluene. This reaction mixture was then heated at 130°-140° C. for 3 hours. Upon cooling to room temperature the mixture solidified. This solid was washed with Skelly "B" solvent several times on a Buchner funnel and recrystallized from a Skelly "B"-benzene mixed solvent (20/80). Pale yellow crystals were obtained, m.p. 163°-165° C.

Source