Reaction #74961

Reaction equation

hexachlorocyclopentadiene

p-benzoquinone

→

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

Yield 64.0%

Solvents

toluene

toluene

Conditions

Workup

1. 1
   workup.ADDITIONA mixture of 54.6 g
2. 2
   Temperaturerefluxed gently
3. 3
   Othercompletion of the reaction
4. 4
   Washrinsed with absolute ethanol
5. 5
   Otherdried on the funnel
6. 6
   Othercrystallized from ethanol
7. 7
   Otherof bright yellow dense crystals were obtained
8. 8
   Otherm.p. 189°-193° C. (reported 188° C.)

Procedure

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