Iodine → HCID 12140370, compound

HRID 2356165Notes

Reaction equation

HRID 2356165 reaction equation
[I:1]I.I(O)(=O)(=O)=O.S(=O)(=O)(O)O.[CH2:13]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>O.C(O)(=O)C>[CH2:27]([O:26][C:21]1[CH:22]=[CH:23][C:24]([I:1])=[CH:25][C:20]=1[O:19][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

7

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 65185Metaperiodic acidHCID 43816021,2-Dihexyloxybenzene

Product 1

HCID 12140370HCID 12140370, compoundYield 213.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To 750 mL of glacial acetic acid, 69.3 g (253 mmol) of iodine, 32.8 g (144 mmol) of periodic acid, 150 mL of distilled water, and 22.5 mL of concentrated sulfuric acid were added. The resulting mixture was stirred at ambient temperature for five minutes, and 80.00 g (287 mmol) of 1,2-dihexyloxybenzene was added. Then, the mixture was stirred at 40° C. for 24 hours. The obtained reaction mixture was cooled to ambient temperature, washed with a KOH aqueous solution (1 M, 1.5 L) and 3 L of distilled water, and extracted with 800 mL of chloroform. The organic phase was dried over MgSO4 and the solvent was evaporated. The residue was purified by column chromatography and was then distilled. As a result, 218.6 g of a light brown liquid was obtained.

Workup

  1. stirringThen, the mixture was stirred at 40° C. for 24 hours
  2. customThe obtained reaction mixture
  3. temperaturewas cooled to ambient temperature
  4. washwashed with a KOH aqueous solution (1 M, 1.5 L) and 3 L of distilled water
  5. extractionextracted with 800 mL of chloroform
  6. dry with materialThe organic phase was dried over MgSO4
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography
  9. distillationwas then distilled

Sources & evidence

ORD record
ord-17b9306a34844856a5568463bb09fbbf
Source dataset
uspto-grants-2010_07
Patent number
US07758932B2

Reaction notes

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