Réaction #74961

Équation de réaction

hexachlorocyclopentadiene

p-benzoquinone

→

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

Rendement 64.0%

Solvants

toluene

toluene

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONA mixture of 54.6 g
2. 2
   Températurerefluxed gently
3. 3
   Autrecompletion of the reaction
4. 4
   Lavagerinsed with absolute ethanol
5. 5
   Autredried on the funnel
6. 6
   Autrecrystallized from ethanol
7. 7
   Autreof bright yellow dense crystals were obtained
8. 8
   Autrem.p. 189°-193° C. (reported 188° C.)

Mode opératoire

A mixture of 54.6 g. (0.2 mole) of hexachlorocyclopentadiene, 21.6 g. (0.2 mole) of p-benzoquinone, and 10 ml. of toluene were placed in a 125 ml. round bottom flask and heated for three hours so that the toluene refluxed gently. At the end of this period the reaction mixture suddenly solidified completely, indicating completion of the reaction. The crude product was bright yellow. The damp material was transferred to a Buchner funnel, rinsed with absolute ethanol, dried on the funnel, and crystallized from ethanol. 49 g. of bright yellow dense crystals were obtained, m.p. 189°-193° C. (reported 188° C.). The yield was 64%.

Source