Acetic Acid → 1,2,3,4,9,9-Hexachloro-1,4,4a,6,7,8a-hexahydro-1,4-methanonaphthalene-5,8-dione

HRID 46691

反応式

HRID 46691 の反応式
[Cl:1][C:2]12[C:14]([Cl:16])([Cl:15])[C:5]([Cl:17])([CH:6]3[CH:11]1[C:10](=[O:12])[CH:9]=[CH:8][C:7]3=[O:13])[C:4]([Cl:18])=[C:3]2[Cl:19].C(O)(=O)C.O>[Zn].C(Cl)(Cl)Cl>[Cl:1][C:2]12[C:14]([Cl:15])([Cl:16])[C:5]([Cl:17])([CH:6]3[CH:11]1[C:10](=[O:12])[CH2:9][CH2:8][C:7]3=[O:13])[C:4]([Cl:18])=[C:3]2[Cl:19]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 962WaterHCID 2289471,2,3,4,9,9-Hexachloro-1,4,4A,8A-tetrahydro-1,4-methanonaphthalene-5,8-dione

生成物 1

HCID 203005941,2,3,4,9,9-Hexachloro-1,4,4a,6,7,8a-hexahydro-1,4-methanonaphthalene-5,8-dione

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 6212Chloroform溶媒

反応条件

温度
50 °C

実験手順

38 g. of 1,2,3,4,9,9-hexachloro-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione, prepared as in Example 1, were suspended in 150 ml. of glacial acetic acid and then this mixture was poured into 20 g. of zinc dust suspended in 150 ml. of distilled water. A slight exotherm occurred during stirring and the temperature was maintained at 50° C. for 3 hours by external heating. Then 200 ml. of chloroform were added and stirring was continued for 30 minutes more. The chloroform layer was separated and washed with a saturated sodium carbonate solution and dried over anhydrous magnesium sulfate. Evaporation of the chloroform left a white solid. One recrystallization from methanol gave white crystals, m.p. 169°-170° C. Infrared spectrum showed carbonyl at 1740 cm-1. The nmr indicated two bridgehead protons at 431 Hz (singlet) and four α-protons at 303 Hz and 245 Hz (as a multiplet).

後処理

  1. stirringstirring
  2. customThe chloroform layer was separated
  3. washwashed with a saturated sodium carbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the chloroform
  6. waitleft a white solid
  7. customOne recrystallization from methanol
  8. customgave white crystals, m.p. 169°-170° C

出典と根拠

ORDレコード
ord-53f029cbc50d4263a98ea3b05e2cea99
出典データセット
uspto-grants-1979_11
特許番号
US04174457

関連ノート

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