Quinone → 1,2,3,4,9,9-Hexabromo-1,4-dihydro-1,4-methanonaphthalene-5,8-diol

HRID 1439233

Reaction equation

HRID 1439233 reaction equation
[C:1]1(=[O:8])[CH:6]=[CH:5][C:4](=[O:7])[CH:3]=[CH:2]1.[Br:9][C:10]1[C:14]([Br:16])([Br:15])[C:13]([Br:17])=[C:12]([Br:18])[C:11]=1[Br:19]>C1(C)C=CC=CC=1>[Br:17][C:13]12[C:14]([Br:15])([Br:16])[C:10]([Br:9])([C:6]3[C:1]([OH:8])=[CH:2][CH:3]=[C:4]([OH:7])[C:5]=31)[C:11]([Br:19])=[C:12]2[Br:18]

Participants

4

Reactant 2

HCID 4650QuinoneHCID 2812931,2,3,4,5,5-Hexabromocyclopenta-1,3-diene

Product 1

HCID 203006301,2,3,4,9,9-Hexabromo-1,4-dihydro-1,4-methanonaphthalene-5,8-diol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of benzoquinone, 10.8 g. toluene (40 ml) and 1,2,3,4,5,5-hexabromo-1,3-cyclopentadiene (60 g.) was heated to reflux temperature and refluxed for four hours. At the end of this reaction period a dark solid had formed. This solid was placed on a Buchner funnel and washed with Skelly B solvent and a small amount of methanol. The solid was then recrystallized from benzene and white crystals were obtained, m.p. 204°-206° C.

Workup

  1. temperatureto reflux temperature
  2. temperaturerefluxed for four hours
  3. customAt the end of this reaction period a dark solid
  4. customhad formed
  5. washwashed with Skelly B solvent
  6. customThe solid was then recrystallized from benzene
  7. customwhite crystals were obtained

Sources & evidence

ORD record
ord-dbe85de66fbe49cc93bb8d36c83c7e8c
Source dataset
uspto-grants-1977_11
Patent number
US04058568

Linked notes

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