Methanol → 1,4-Dihydro-1,2,3,4,9,9-hexachloro-1,4-methanonaphthalene-5,8-diol

HRID 1580332Notes

Reaction equation

HRID 1580332 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].CO>N1C=CC=CC=1>[Cl:1][C:2]12[C:14]([Cl:15])([Cl:16])[C:5]([Cl:17])([C:6]3[C:7]([OH:13])=[CH:8][CH:9]=[C:10]([OH:12])[C:11]=31)[C:4]([Cl:18])=[C:3]2[Cl:19]

Participants

4

Reactant 2

HCID 887MethanolHCID 2289471,2,3,4,9,9-Hexachloro-1,4,4A,8A-tetrahydro-1,4-methanonaphthalene-5,8-dione

Product 1

HCID 2289461,4-Dihydro-1,2,3,4,9,9-hexachloro-1,4-methanonaphthalene-5,8-diol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

50 g. of 1,2,3,4,9,9-hexachloro-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione were dissolved in 300 ml. of methanol and 3 g. of pyridine were added. The mixture was refluxed until the yellow color disappeared (about 5 hours). Upon cooling to 5°-7°C., white crystals separated. One recrystallization from methanol gave white crystals, m.p. 186°C. The yield was almost quantitative.

Workup

  1. temperatureThe mixture was refluxed until the yellow color
  2. custom(about 5 hours)
  3. temperatureUpon cooling to 5°-7°C.
  4. customwhite crystals separated
  5. customOne recrystallization from methanol
  6. customgave white crystals, m.p. 186°C

Sources & evidence

ORD record
ord-3c459bd9ed854546b0fd016d5d2bb96a
Source dataset
uspto-grants-1976_01
Patent number
US03932525

Reaction notes

Loading…