Iodine → HCID 178439067, compound

HRID 342355Notes

Reaction equation

HRID 342355 reaction equation
S(=O)(=O)(O)O.[CH2:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C@H:17]2[CH2:22][CH2:21][C@H:20]([CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:19][CH2:18]2)=[CH:11][CH:10]=1)[CH2:7][CH3:8].II.[I:33](O)(=O)=O>O.C(Cl)(Cl)(Cl)Cl.C(O)(=O)C>[CH2:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C@H:17]2[CH2:22][CH2:21][C@H:20]([CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([I:33])=[CH:29][CH:30]=3)[CH2:19][CH2:18]2)=[CH:11][CH:10]=1)[CH2:7][CH3:8]

Participants

8

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 24345Iodic acidHCID 178439065HCID 178439065, compound

Product 1

HCID 178439067HCID 178439067, compoundYield 46.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixed solution comprising 250 ml of acetic acid, 25 ml of carbon tetrachloride, 25 ml of concentrated sulfuric acid, and 50 ml of water were added 26 g of the (2-(trans-4-(2-(4-n-propylphenyl)ethyl)cyclohexyl)ethyl)benzene mentioned above, 10 g of iodine, and 8.4 g of iodic acid, and they were stirred under a reflux for 2 hours. After cooled, they were 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, and then recrystallized from heptane to obtain 10.3 g of 4-(2-(trans-4-(2-(4-n-propylphenyl)ethyl)cyclohexyl)ethyl)iodobenzene.

Workup

  1. temperaturea reflux for 2 hours
  2. temperatureAfter cooled
  3. washthey were 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. customrecrystallized from heptane

Sources & evidence

ORD record
ord-3bde00431ba4486295dd8983c9916ee5
Source dataset
uspto-grants-1999_01
Patent number
US05858275

Reaction notes

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