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 1733190Notes

Reaction equation

HRID 1733190 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° C.-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-d62744d930b74d6798b8e090279db98e
Source dataset
uspto-grants-1980_12
Patent number
US04240974

Reaction notes

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