Benzenesulfonyl chloride → 1,2,3,4,9,9-Hexachloro-1,4-dihydro-6-(phenylsulfonyl)-1,4-methanonaphthalene-5,8-diol

HRID 46686Notes

Reaction equation

HRID 46686 reaction equation
[Cl:1][C:2]12[C:14]([Cl:16])([Cl:15])[C:5]([Cl:17])([C:6]3[C:7](=[O:13])[CH:8]=[CH:9][C:10](=[O:12])[C:11]=31)[C:4]([Cl:18])=[C:3]2[Cl:19].[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[Cl:1][C:2]12[C:14]([Cl:15])([Cl:16])[C:5]([Cl:17])([C:6]3[C:7]([OH:13])=[C:8]([S:26]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)(=[O:28])=[O:27])[CH:9]=[C:10]([OH:12])[C:11]=31)[C:4]([Cl:18])=[C:3]2[Cl:19]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 4095651,2,3,4,9,9-Hexachloro-1,4-dihydro-1,4-methanonaphthalene-5,8-dione

Product 1

HCID 203006021,2,3,4,9,9-Hexachloro-1,4-dihydro-6-(phenylsulfonyl)-1,4-methanonaphthalene-5,8-diol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

38 g. of 1,2,3,4,9,9-hexachloro-1,4-dihydro-1,4-methanonaphthalene-5,8-dione, prepared as in Example 3, were dissolved in 200 ml. of ethanol and 18 g. of freshly generated benzenesulfonyl chloride were added. This mixture was refluxed for 5 hours and a white precipitate formed. The white solid was filtered off while hot and was recrystallized from benzene yielding white crystals, m.p. 215°-216° C.

Workup

  1. dissolutionwere dissolved in 200 ml
  2. temperatureThis mixture was refluxed for 5 hours
  3. customa white precipitate formed
  4. filtrationThe white solid was filtered off while hot and
  5. customwas recrystallized from benzene yielding white crystals, m.p. 215°-216° C.

Sources & evidence

ORD record
ord-b698ae4c283443b184e5d6b8910eaf3c
Source dataset
uspto-grants-1979_11
Patent number
US04174457

Reaction notes

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