Sulfuric Acid → 1,3,5-Triiodo-2,4,6-triacetoxymethylbenzene

HRID 382998Notes

Reaction equation

HRID 382998 reaction equation
[I:1][C:2]1[C:7]([CH3:8])=[C:6]([I:9])[C:5]([CH3:10])=[C:4]([I:11])[C:3]=1[CH3:12].C([O:16][C:17](=[O:19])[CH3:18])(=O)C.S(=O)(=O)(O)O.[Mn]([O-])(=O)(=O)=O.[K+]>C(O)(=O)C>[I:1][C:2]1[C:3]([CH2:12][O:19][C:17](=[O:16])[CH3:18])=[C:4]([I:11])[C:5]([CH2:10][O:19][C:17](=[O:16])[CH3:18])=[C:6]([I:9])[C:7]=1[CH2:8][O:16][C:17](=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 516875Potassium PermanganateHCID 6356131,3,5-Triiodo-2,4,6-trimethylbenzene

Product 1

HCID 235425991,3,5-Triiodo-2,4,6-triacetoxymethylbenzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Triiodomesitylene (19.5 g, 39 mmol) was added to glacial acetic acid (200 ml) containing acetic anhydride (400 ml) and concentrated sulfuric acid (40 ml). Solid potassium permanganate (24.6 g, 156 mmol) was then added in small portions over a period of 3 h. After stirring for 16 h, the solvent was evaporated and water (200 ml) was added. The aqueous suspension was extracted with dichloromethane (250 ml) and the organic phase was washed with water (3×50 ml), dried (MgSO4) and evaporated. The solid residue was suspended in acetone and the white crystalline product was collected by filtration. Yield: 9.3 g (35%).

Workup

  1. customthe solvent was evaporated
  2. additionwater (200 ml) was added
  3. extractionThe aqueous suspension was extracted with dichloromethane (250 ml)
  4. washthe organic phase was washed with water (3×50 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. filtrationthe white crystalline product was collected by filtration

Sources & evidence

ORD record
ord-47d25f156e93415b91b1a5846fb1306d
Source dataset
uspto-grants-2001_10
Patent number
US06310243B1

Reaction notes

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