Reaction #74963

ord-33984a9f0bc7469b92c1d7e96b01d0d9

Reaction equation

ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl
Hexachlorocyclopentadiene
CC(C)(C)C1=CC(=O)C=CC1=O
tert-butyl-p-benzoquinone
→
CC(C)(C)C1=CC(=O)C2C(C1=O)C1(Cl)C(Cl)=C(Cl)C2(Cl)C1(Cl)Cl
6-tert-butyl-1,2,3,4,9,9-hexachloro-1,4,4a,8a-tetrahydro-1,4methanonaphthalene-5,8-dione

Reactants

ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl
Hexachlorocyclopentadiene
CC(C)(C)C1=CC(=O)C=CC1=O
tert-butyl-p-benzoquinone

Reagents

None

Solvents

Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    WashThe solid was washed with methanol
  2. 2
    Otherrecrystallized from benzene
  3. 3
    OtherYellow crystals were obtained melting at 124°-125° C.

Procedure

Hexachlorocyclopentadiene, 40 g., and 15.4 g. of tert-butyl-p-benzoquinone were dissolved in 300 ml. of toluene and refluxed for four hours. The solution solidified upon cooling to room temperature. The solid was washed with methanol and recrystallized from benzene. Yellow crystals were obtained melting at 124°-125° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04174457uspto-grants-1979_11