Sulfuric Acid → 2,3,6,7,10,11-Hexamethoxytriphenylene

HRID 1682408Notes

Reaction equation

HRID 1682408 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].S(=O)(=O)(O)O>O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+3].S([O-])([O-])(=O)=O.S([O-])([O-])(=O)=O.[Fe+3]>[CH3:1][O:2][C:3]1[C:4]([O:9][CH3:10])=[CH:5][C:6]2[C:7]3[C:6](=[CH:5][C:4]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:8]=3)[C:7]3[C:6](=[CH:5][C:4]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:8]=3)[C:7]=2[CH:8]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 7043Veratrole

Product 1

HCID 46073632,3,6,7,10,11-HexamethoxytriphenyleneYield 83%

Reagents, catalysts & solvents 2

HCID 26260Ferric sulfate hexahydrateCatalyst2×HCID 962WaterSolvent

Procedure

In a 2-liter three-necked flask chilled with ice, 455 g of iron(III) sulfate hexahydrate and 193 ml of ice-water were placed, and vigorously stirred to completely dissolve iron(III) sulfate hexa-hydrate in water. Thereafter, 58.7 g of 1,2-dimethoxybenzene was further added to the solution and 882 ml of concentrated sulfuric acid was gradually added with cooling to prepare a mixture. After reaction of 24 hours, 9 liter of ice-water was gradually added to the reaction mixture. After stirring of 5 hours, the reaction mixture was filtered through a glass filter to obtain crude crystals of the above compound (TP-A) of 48.1 g (yield: 83%)

Workup

  1. additionwas gradually added
  2. temperaturewith cooling
  3. customto prepare a mixture
  4. additionwas gradually added to the reaction mixture
  5. filtrationthe reaction mixture was filtered through a glass
  6. filtrationfilter
  7. customto obtain crude crystals of the above compound (TP-A) of 48.1 g (yield: 83%)

Sources & evidence

ORD record
ord-9ad288909d70403fa13a51233e024b67
Source dataset
uspto-grants-1997_06
Patent number
US05635105

Reaction notes

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