Hexachlorocyclopentadiene → 1,2,3,4,9,9-Hexachloro-1,4,4a,8a-tetrahydro-6-methyl-1,4-methanonaphthalene-5,8-dione

HRID 1439239Notes

Reaction equation

HRID 1439239 reaction equation
[CH3:1][C:2]1[C:3](=[O:9])[CH:4]=[CH:5][C:6](=[O:8])[CH:7]=1.[Cl:10][C:11]1([Cl:20])[C:15]([Cl:16])=[C:14]([Cl:17])[C:13]([Cl:18])=[C:12]1[Cl:19]>C1(C)C=CC=CC=1>[Cl:16][C:15]12[C:11]([Cl:10])([Cl:20])[C:12]([Cl:19])([CH:4]3[CH:5]1[C:6](=[O:8])[CH:7]=[C:2]([CH3:1])[C:3]3=[O:9])[C:13]([Cl:18])=[C:14]2[Cl:17]

Participants

4

Reactant 2

HCID 6478HexachlorocyclopentadieneHCID 11122Methyl-1,4-benzoquinone

Product 1

HCID 203006151,2,3,4,9,9-Hexachloro-1,4,4a,8a-tetrahydro-6-methyl-1,4-methanonaphthalene-5,8-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
135 °C

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.

Workup

  1. additionwas added 20 ml
  2. temperatureUpon cooling to room temperature the mixture
  3. washThis solid was washed with Skelly "B" solvent several times on a Buchner funnel
  4. customrecrystallized from a Skelly "B"-benzene mixed solvent (20/80)
  5. customPale yellow crystals were obtained

Sources & evidence

ORD record
ord-ac7dec215c1f40e68a73d07ba00ce620
Source dataset
uspto-grants-1977_11
Patent number
US04058568

Reaction notes

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