Methanol → 1,2,3,4,9,9-Hexachloro-1,4-dihydro-6-methyl-1,4-methanonaphthalene-5,8-diol

HRID 1679336Notes

Reaction equation

HRID 1679336 reaction equation
[Cl:1][C:2]12[C:15]([Cl:17])([Cl:16])[C:5]([Cl:18])([CH:6]3[CH:11]1[C:10](=[O:12])[CH:9]=[C:8]([CH3:13])[C:7]3=[O:14])[C:4]([Cl:19])=[C:3]2[Cl:20].CO>N1C=CC=CC=1>[Cl:1][C:2]12[C:15]([Cl:16])([Cl:17])[C:5]([Cl:18])([C:6]3[C:7]([OH:14])=[C:8]([CH3:13])[CH:9]=[C:10]([OH:12])[C:11]=31)[C:4]([Cl:19])=[C:3]2[Cl:20]

Participants

4

Reactant 2

HCID 887MethanolHCID 203006151,2,3,4,9,9-Hexachloro-1,4,4a,8a-tetrahydro-6-methyl-1,4-methanonaphthalene-5,8-dione

Product 1

HCID 203626361,2,3,4,9,9-Hexachloro-1,4-dihydro-6-methyl-1,4-methanonaphthalene-5,8-diol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

30 g. of 1,2,3,4,9,9-hexachloro-1,4,4a,8a-tetrahydro-6-methyl-1,4-methanonaphthalene-5,8-dione, prepared according to Example 45, were suspended in 150 ml. of methanol. 2 ml. of pyridine were added and the mixture was refluxed for 4 hours. Upon cooling in an ice-water bath, a crude white solid formed. This solid was recrystallized from methanol and white crystals were obtained, m.p. 159°-161° C.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. temperatureUpon cooling in an ice-water bath
  3. customa crude white solid formed
  4. customThis solid was recrystallized from methanol
  5. customwhite crystals were obtained

Sources & evidence

ORD record
ord-6c8040a7476f4804b56d1e9ca5b9e478
Source dataset
uspto-grants-1978_03
Patent number
US04080408

Reaction notes

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