6-Tert-butyl-1,2,3,4,9,9-hexachloro-1,4,4a,8a-tetrahydro-1,4methanonaphthalene-5,8-dione → 6-Tert-butyl-1,2,3,4,9,9-hexachloro-1,4-dihydro-1,4-methanonaphthalene-5,8-diol

HRID 436589Notes

Reaction equation

HRID 436589 reaction equation
[C:1]([C:5]1[C:6](=[O:23])[CH:7]2[CH:12]([C:13](=[O:15])[CH:14]=1)[C:11]1([Cl:19])[C:16]([Cl:18])([Cl:17])[C:8]2([Cl:22])[C:9]([Cl:21])=[C:10]1[Cl:20])([CH3:4])([CH3:3])[CH3:2]>N1C=CC=CC=1.CO>[C:1]([C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:11]3([Cl:19])[C:16]([Cl:17])([Cl:18])[C:8]([Cl:22])([C:9]([Cl:21])=[C:10]3[Cl:20])[C:7]=2[C:6]=1[OH:23])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 203006266-Tert-butyl-1,2,3,4,9,9-hexachloro-1,4,4a,8a-tetrahydro-1,4methanonaphthalene-5,8-dione

Product 1

HCID 203006376-Tert-butyl-1,2,3,4,9,9-hexachloro-1,4-dihydro-1,4-methanonaphthalene-5,8-diol

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 887MethanolSolvent

Procedure

10 g. of 6-tert-butyl-1,2,3,4,9,9-hexachloro-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione, prepared according to Example 8, were dissolved in 50 ml. of methanol. A few drops of pyridine were added and the solution was refluxed strongly for three hours. Evaporation of the methanol yielded an oily material which upon recrystallization twice from Skelly B gave white needle crystals melting at 96°-98° C.

Workup

  1. dissolutionwere dissolved in 50 ml
  2. temperaturethe solution was refluxed strongly for three hours
  3. customEvaporation of the methanol
  4. customyielded an oily material which
  5. customupon recrystallization twice from Skelly B

Sources & evidence

ORD record
ord-9d97a6d6854f4d529ef5ee319c7b9e46
Source dataset
uspto-grants-1977_02
Patent number
US04009200

Reaction notes

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