Hexachlorocyclopentadiene → 6-Tert-butyl-1,2,3,4,9,9-hexachloro-1,4,4a,8a-tetrahydro-1,4methanonaphthalene-5,8-dione

HRID 1679325Notes

Reaction equation

HRID 1679325 reaction equation
[Cl:1][C:2]1([Cl:11])[C:6]([Cl:7])=[C:5]([Cl:8])[C:4]([Cl:9])=[C:3]1[Cl:10].[C:12]([C:16]1[C:17](=[O:23])[CH:18]=[CH:19][C:20](=[O:22])[CH:21]=1)([CH3:15])([CH3:14])[CH3:13]>C1(C)C=CC=CC=1>[C:12]([C:16]1[C:17](=[O:23])[CH:18]2[CH:19]([C:20](=[O:22])[CH:21]=1)[C:3]1([Cl:10])[C:2]([Cl:11])([Cl:1])[C:6]2([Cl:7])[C:5]([Cl:8])=[C:4]1[Cl:9])([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 6478HexachlorocyclopentadieneHCID 19211tert-Butyl-1,4-benzoquinone

Product 1

HCID 203006266-Tert-butyl-1,2,3,4,9,9-hexachloro-1,4,4a,8a-tetrahydro-1,4methanonaphthalene-5,8-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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.

Workup

  1. washThe solid was washed with methanol
  2. customrecrystallized from benzene
  3. customYellow crystals were obtained melting at 124°-125° C.

Sources & evidence

ORD record
ord-8b60df5325264b26a5cb1fb4ea465ad1
Source dataset
uspto-grants-1978_03
Patent number
US04080408

Reaction notes

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