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

HRID 436584

Reaction equation

HRID 436584 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

Sources & evidence

ORD record
ord-bebd30c4a31c439c8ca2e9df4fd11cbf
Source dataset
uspto-grants-1977_02
Patent number
US04009200

Linked notes

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