Toluene → 1,4-Dihydro-1,2,3,4,9,9-hexachloro-1,4-methanonaphthalene-5,8-diol

HRID 1973773Notes

Reaction equation

HRID 1973773 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>C(O)C>[Cl:7][C:6]12[C:2]([Cl:11])([Cl:1])[C:3]([Cl:10])([C:17]3[C:12]([OH:19])=[CH:13][CH:14]=[C:15]([OH:18])[C:16]=31)[C:4]([Cl:9])=[C:5]2[Cl:8]

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 4650QuinoneHCID 6478Hexachlorocyclopentadiene

Product 1

HCID 2289461,4-Dihydro-1,2,3,4,9,9-hexachloro-1,4-methanonaphthalene-5,8-diol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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 3 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 Buchner funnel, raised 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. customdried on the funnel
  5. customcrystallized from ethanol
  6. customof bright yellow dense crystals were obtained
  7. customm.p. 189° -193° C. (reported 188° C.)

Sources & evidence

ORD record
ord-dccfc7c4b5834126a7d5c2ecb7f1c28c
Source dataset
uspto-grants-1976_12
Patent number
US03998913

Reaction notes

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