Quinone → 1,2,3,4,9,9-Hexachloro-1,4,4A,8A-tetrahydro-1,4-methanonaphthalene-5,8-dione

HRID 1733183Notes

Reaction equation

HRID 1733183 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]1(=[O:19])[CH:17]=[CH:16][C:15](=[O:18])[CH:14]=[CH:13]1>C1(C)C=CC=CC=1>[Cl:7][C:6]12[C:2]([Cl:11])([Cl:1])[C:3]([Cl:10])([CH:17]3[CH:16]1[C:15](=[O:18])[CH:14]=[CH:13][C:12]3=[O:19])[C:4]([Cl:9])=[C:5]2[Cl:8]

Participants

4

Reactant 2

HCID 4650QuinoneHCID 6478Hexachlorocyclopentadiene

Product 1

HCID 2289471,2,3,4,9,9-Hexachloro-1,4,4A,8A-tetrahydro-1,4-methanonaphthalene-5,8-dioneYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 54.6 g. (0.2 mole) of hexachlorocyclopentadiene, 21.6 g. (0.2 mole) of p-benzoquinone, and 10 ml. of toluene were placed in a 125 ml. round bottom flask and heated for three hours so that the toluene refluxed gently. At the end of this period the reaction mixture suddenly solidified completely, indicating completion of the reaction. The crude product was bright yellow. The damp material was transferred to a Buuchner funnel, rinsed with absolute ethanol, dried on the funnel, and crystallized from ethanol. 49 g. of bright yellow dense crystals were obtained, m.p. 189°-193° C. (reported 188° C.). The yield was 64%.

Workup

  1. additionA mixture of 54.6 g
  2. temperaturerefluxed gently
  3. customcompletion of the reaction
  4. washrinsed with absolute ethanol
  5. customdried on the funnel
  6. customcrystallized from ethanol
  7. customof bright yellow dense crystals were obtained
  8. customm.p. 189°-193° C. (reported 188° C.)

Sources & evidence

ORD record
ord-85a3fd0e31a240b3864a31e8f3c2a050
Source dataset
uspto-grants-1980_12
Patent number
US04240974

Reaction notes

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