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

HRID 1597714Notes

Reaction equation

HRID 1597714 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15]>[Fe](Cl)(Cl)Cl>[CH3:6][O:7][C:8]1[C:9]([O:14][CH3:15])=[CH:10][C:11]2[C:12]3[C:11](=[CH:10][C:9]([O:14][CH3:15])=[C:8]([O:7][CH3:6])[CH:13]=3)[C:12]3[C:11](=[CH:10][C:9]([O:14][CH3:15])=[C:8]([O:7][CH3:6])[CH:13]=3)[C:12]=2[CH:13]=1

Participants

4

Reactant 2

HCID 1118Sulfuric Acid3×HCID 7043Veratrole

Product 1

HCID 46073632,3,6,7,10,11-HexamethoxytriphenyleneYield 43%

Reagents, catalysts & solvents 1

HCID 24380Iron chloride (FeCl3)Catalyst

Procedure

In a 2-liter three-necked flask cooled with ice, 135 ml of ice water was placed, and 490 ml of concentrated sulfuric acid was gradually added to the ice water with stirring to prepare a sulfuric acid solution. Subsequently, 150 g of iron(III) chloride was added to the sulfuric acid solution at room temperature, and after reaction of 1 hour, 30 g of 1,2-dimethoxybenzene was further added to prepare a reaction mixture. After reaction of 3 hours, the reaction mixture was cooled with ice, and 1 liter of ice water was gradually added to the reaction mixture. After stirring of 1 hour, the reaction mixture was filtered through a glass filter to obtain crude crystals of the above compound (a) of 13 g (yield: 43%).

Workup

  1. additionwas further added
  2. customto prepare a reaction mixture
  3. customAfter reaction of 3 hours
  4. additionwas gradually added to the reaction mixture
  5. stirringAfter stirring of 1 hour
  6. filtrationthe reaction mixture was filtered through a glass
  7. filtrationfilter

Sources & evidence

ORD record
ord-64f0567a47d9463b9ca53778e37ac165
Source dataset
uspto-grants-1998_04
Patent number
US05736067

Reaction notes

Loading…