Iodine → HCID 12140370, compound

HRID 1442475Notes

Reaction equation

HRID 1442475 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]>C(O)(=O)C.O>[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

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 to 750 mL of glacial acetic acid and stirred for 5 minutes at room temperature followed by the addition of 80.00 g (287 mmol) of 1,2-dihexyloxybenzene and stirring for 24 hours at 40° C. The resulting reaction mixture was cooled to room temperature, washed with aqueous KOH solution (1 M, 1.5 L) and 3 L of distilled water, and then extracted with 800 mL of chloroform. The organic phase was dried with MgSO4 followed by distilling off the solvent. The residue was purified by column chromatography followed by distilling to obtain 218.6 g of a light brown liquid.

Workup

  1. stirringstirring for 24 hours at 40° C
  2. customThe resulting reaction mixture
  3. temperaturewas cooled to room temperature
  4. washwashed with aqueous KOH 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 with MgSO4
  7. distillationby distilling off the solvent
  8. customThe residue was purified by column chromatography
  9. distillationby distilling

Sources & evidence

ORD record
ord-a0eab64398704de29c1bfc77a6859e75
Source dataset
uspto-grants-2010_02
Patent number
US07658979B2

Reaction notes

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