Acetic Acid → 1,2,3,4,9,9-Hexachloro-1,4-dihydro-5,8-dihydroxy-1,4-methanonaphth-6-yl methyl ketone

HRID 46687Notes

Reaction equation

HRID 46687 reaction equation
[Cl:1][C:2]12[C:14]([Cl:16])([Cl:15])[C:5]([Cl:17])([C:6]3[C:7]([OH:13])=[CH:8][CH:9]=[C:10]([OH:12])[C:11]=31)[C:4]([Cl:18])=[C:3]2[Cl:19].[C:20](O)(=[O:22])[CH3:21]>>[CH3:21][C:20]([C:8]1[C:7]([OH:13])=[C:6]2[C:11](=[C:10]([OH:12])[CH:9]=1)[C:2]1([Cl:1])[C:14]([Cl:15])([Cl:16])[C:5]2([Cl:17])[C:4]([Cl:18])=[C:3]1[Cl:19])=[O:22]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 2289461,4-Dihydro-1,2,3,4,9,9-hexachloro-1,4-methanonaphthalene-5,8-diol

Product 1

HCID 203006231,2,3,4,9,9-Hexachloro-1,4-dihydro-5,8-dihydroxy-1,4-methanonaphth-6-yl methyl ketone

Conditions

Temperature
40 °C

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.

Workup

  1. additionof boron trifluoride-diethyl ether complex were added
  2. temperatureThis mixture was heated at 100°-105° C. for 5 hours
  3. customrecrystallization from benzene white crystals
  4. customwere obtained

Sources & evidence

ORD record
ord-965fa8138b4040f9a30b15e79f0af500
Source dataset
uspto-grants-1979_11
Patent number
US04174457

Reaction notes

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