Réaction #74966

Équation de réaction

1,2,3,4,6,9,9-heptachloro-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione

methanol

→

1,2,3,4,6,9,9-heptachloro-1,4-dihydro-1,4-methanonaphthalene-5,8-diol

Solvants

pyridine

Conditions de réaction

Traitement

1. 1
   Autreprepared
2. 2
   AutreThe resulting reaction mixture
3. 3
   workup.STIRRINGwas continuously stirred
4. 4
   Températurerefluxed vigorously for 8.5 hours
5. 5
   TempératureAfter cooling the mixture to 0° C.
6. 6
   Filtrationit was filtered
7. 7
   Lavagethe crude solid was washed with cold Skellysolve
8. 8
   AutreThe product was recrystallized from a mixture of 1000 ml

Mode opératoire

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##

Source