Benzenesulfinic acid → 1,2,3,4,9,9-Hexachloro-1,4,4a,6,7,8a-hexahydro-6-phenylsulfonyl-1,4-methanonaphthalene-5,8-dione

HRID 436591

Reaction equation

HRID 436591 reaction equation
[Cl:1][C:2]12[C:14]([Cl:16])([Cl:15])[C:5]([Cl:17])([CH:6]3[CH:11]1[C:10](=[O:12])[CH:9]=[CH:8][C:7]3=[O:13])[C:4]([Cl:18])=[C:3]2[Cl:19].[C:20]1([S:26]([OH:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O.C1C=CC=CC=1>[Cl:1][C:2]12[C:14]([Cl:15])([Cl:16])[C:5]([Cl:17])([CH:6]3[CH:11]1[C:10](=[O:12])[CH2:9][CH:8]([S:26]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:28])=[O:27])[C:7]3=[O:13])[C:4]([Cl:18])=[C:3]2[Cl:19]

Participants

5

Reactant 2

HCID 12057Benzenesulfinic acidHCID 2289471,2,3,4,9,9-Hexachloro-1,4,4A,8A-tetrahydro-1,4-methanonaphthalene-5,8-dione

Product 1

HCID 203006051,2,3,4,9,9-Hexachloro-1,4,4a,6,7,8a-hexahydro-6-phenylsulfonyl-1,4-methanonaphthalene-5,8-dioneYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 241BenzeneSolvent

Procedure

38 g. of 1,2,3,4,9,9-hexachloro-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione, prepared as in Example 1, were dissolved in 250 ml. of benzene, 15 g. of freshly generated benzene sulfinic acid were added and then a few drops of water were added. This reaction mixture was heated at 40°-45° C. for 12 hours and then the benzene was evaporated. The white solid residue obtained was recrystallized from benzene twice and yielded white crystals, m.p. 157°-158° C. The yield was about 88%.

Workup

  1. dissolutionwere dissolved in 250 ml
  2. temperatureThis reaction mixture was heated at 40°-45° C. for 12 hours
  3. customthe benzene was evaporated
  4. customThe white solid residue obtained
  5. customwas recrystallized from benzene twice
  6. customyielded white crystals, m.p. 157°-158° C

Sources & evidence

ORD record
ord-5c20fb06b8024b4f8d81fc500a91d74b
Source dataset
uspto-grants-1977_02
Patent number
US04009200

Linked notes

Loading…