Reaction #74974

Reaction equation

Hexachlorocyclopentadiene

1,4-naphthoquinone

→

1,2,3,4,11,11-hexachloro-1,4,4a,9a-tetrahydro-1,4-methanoanthracene-9,10-dione

Solvents

toluene

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureto reflux temperature
3. 3
   Temperaturemaintained at this temperature for 4 hours
4. 4
   Extractionextracting the excess hexachlorocyclopentadiene with Skelly "B" solvent
5. 5
   OtherThis crude brown solid was recrystallized repeatedly from benzene/Skelly "B" mix-solvent (70/30)
6. 6
   Otherto yield white crystals, m.p. 116°-118° C.

Procedure

Hexachlorocyclopentadiene (60 g.), 1,4-naphthoquinone (31.6 g.), and 30 ml. of toluene were mixed, heated to reflux temperature, and maintained at this temperature for 4 hours. After cooling to room temperature and extracting the excess hexachlorocyclopentadiene with Skelly "B" solvent, the mixture solidified slowly. This crude brown solid was recrystallized repeatedly from benzene/Skelly "B" mix-solvent (70/30) to yield white crystals, m.p. 116°-118° C.

Source