Reaktion #429529

Reaktionsgleichung

sulfuric acid

iodine

iodic acid

(trans-4-(2-(trans-4-n-propylcyclohexyl)ethyl)cyclohexyl)benzene

→

4-(trans-4-(2-(trans-4-n-propylcyclohexyl)ethyl)cyclohexyl)iodobenzene

Ausbeute 21.2%

Lösungsmittel

water

carbon tetrachloride

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperatura reflux for 2 hours
2. 2
   TemperaturAfter cooled
3. 3
   Waschenthe mixture was washed with a saturated aqueous solution of sodium thiosulfate
4. 4
   WaschenOrganic layer was washed with water
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off under a reduced pressure
7. 7
   Sonstigeto obtain a yellow-brown oily product
8. 8
   SonstigeThis product was purified by a column chromatography over an alumina
9. 9
   SonstigeFurther, it was recrystallized from heptane

Vorschrift

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.

Quelle