Methanol → HCID 20300597, compound

HRID 46688Notes

Reaction equation

HRID 46688 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]([Cl: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]([Cl: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 203006281,2,3,4,6,9,9-Heptachloro-1,4,4a, 8a-tetrahydro-1,4-methanonaphthalene-5,8-dione

Product 1

HCID 20300597HCID 20300597, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 256 grams (0.62 mol.) of 1,2,3,4,6,9,9-heptachloro-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione, prepared according to Example 24, and 500 ml. of methanol in a 2 liter reaction flask was stirred at room temperature while air in the reaction vessel was swept out with nitrogen. Six ml. of pyridine was then added to the liquid-solid mixture. The resulting reaction mixture was continuously stirred, and refluxed vigorously for 8.5 hours. After cooling the mixture to 0° C., it was filtered, and the crude solid was washed with cold Skellysolve. Yield 121 grams. The product was recrystallized from a mixture of 1000 ml. of Skellysolve and 250 ml. of acetone. M.P. 120.5°-122° C. The product has the following structure: ##STR57##

Workup

  1. customprepared
  2. customThe resulting reaction mixture
  3. stirringwas continuously stirred
  4. temperaturerefluxed vigorously for 8.5 hours
  5. temperatureAfter cooling the mixture to 0° C.
  6. filtrationit was filtered
  7. washthe crude solid was washed with cold Skellysolve
  8. customThe product was recrystallized from a mixture of 1000 ml

Sources & evidence

ORD record
ord-ea2aaea7fcb84ecf97673d17fa69c1c4
Source dataset
uspto-grants-1979_11
Patent number
US04174457

Reaction notes

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