Iodine → HCID 178447972, Verbindung

HRID 342347

Reaktionsgleichung

Reaktionsgleichung von HRID 342347
S(=O)(=O)(O)O.[CH2:6]([C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][CH2:16][C@H:17]2[CH2:22][CH2:21][C@H:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)[CH2:11][CH2:10]1)[CH2:7][CH3:8].II.[I:31](O)(=O)=O>O.C(Cl)(Cl)(Cl)Cl.C(O)(=O)C>[CH2:6]([C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][CH2:16][C@H:17]2[CH2:22][CH2:21][C@H:20]([C:23]3[CH:24]=[CH:25][C:26]([I:31])=[CH:27][CH:28]=3)[CH2:19][CH2:18]2)[CH2:11][CH2:10]1)[CH2:7][CH3:8]

Komponenten

8

Edukt 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 24345Iodic acidHCID 178447967HCID 178447967, Verbindung

Produkt 1

HCID 178447972HCID 178447972, VerbindungAusbeute 21,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a mixed solution comprising 500 ml of acetic acid, 50 ml of carbon tetrachloride, 50 ml of concentrated sulfuric acid, and 100 ml of water were added 58.5 g of the (trans-4-(2-(trans-4-n-propylcyclohexyl)ethyl)cyclohexyl)benzene mentioned above, 22.1 g of iodine, and 18.4 g of iodic acid, and the mixture was stirred under a reflux for 2 hours. After cooled, the mixture was washed with a saturated aqueous solution of sodium thiosulfate. Organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under a reduced pressure to obtain a yellow-brown oily product. This product was purified by a column chromatography over an alumina by using heptane as an eluent. Further, it was recrystallized from heptane to obtain 9.7 g of 4-(trans-4-(2-(trans-4-n-propylcyclohexyl)ethyl)cyclohexyl)iodobenzene.

Aufarbeitung

  1. temperaturea reflux for 2 hours
  2. temperatureAfter cooled
  3. washthe mixture was washed with a saturated aqueous solution of sodium thiosulfate
  4. washOrganic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under a reduced pressure
  7. customto obtain a yellow-brown oily product
  8. customThis product was purified by a column chromatography over an alumina
  9. customFurther, it was recrystallized from heptane

Quellen und Nachweise

ORD-Eintrag
ord-41560168c797400e9cb09659ed435bd3
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05858275

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