Reaction #74965

Reaction equation

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

acetic acid

→

1,2,3,4,9,9-hexachloro-1,4-dihydro-5,8-dihydroxy-1,4-methanonaphth-6-yl methyl ketone

Conditions

Workup

1. 1
   workup.ADDITIONof boron trifluoride-diethyl ether complex were added
2. 2
   TemperatureThis mixture was heated at 100°-105° C. for 5 hours
3. 3
   Otherrecrystallization from benzene white crystals
4. 4
   Otherwere obtained

Procedure

76 g. of 1,2,3,4,9,9-hexachloro-1,4-dihydro-1,4-methanonaphthalene-5,8-diol, prepared according to Example 2, were suspended in 100 ml. of acetic acid and then 20 ml. of boron trifluoride-diethyl ether complex were added. This mixture was heated at 100°-105° C. for 5 hours. After being cooled to 40° C., the mixture was poured into ice water. After repeated recrystallization from benzene white crystals were obtained, m.p. 135°-140° C.

Source