Veratrole → 2,3,6,7,10,11-Hexamethoxytriphenylene

HRID 1925789Notes

Reaction equation

HRID 1925789 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>[OH2:2].[OH:9][C:4]1[C:3]([OH:2])=[CH:8][C:7]2[C:6]3[C:5](=[CH:4][C:3]([OH:2])=[C:8]([OH:2])[CH:7]=3)[C:6]3[C:7](=[CH:8][C:3]([OH:2])=[C:4]([OH:9])[CH:5]=3)[C:6]=2[CH:5]=1.[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

4

Reactant 1

HCID 7043Veratrole

Product 2

HCID 46073632,3,6,7,10,11-HexamethoxytriphenyleneYield 240.1%HCID 569245442,3,6,7,10,11-Hexahydroxytriphenylene hydrate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A type B crystal of 2,3,6,7,10,11-hexahydroxytriphenylene monohydrate was synthesized according to the process described in Synthesis, 477, 1994 and JP-A-8-119894. Namely, 1,2-dimethoxybenzene (31.78 g, 0.23 moles) and anhydrous ferric chloride (120 g, 0.74 moles) were dissolved in 70% sulfuric acid, and the solution was reacted at 25° C. for 24 hours with stirring. After completion of the reaction, the solution was poured into ice water (500 g), and the precipitated crystal was collected by filtration. After the resultant crystal was washed with water (1 L), and then dried to give pale purple colored 2,3,6,7,10,11-hexamethoxytriphenylene (28.2 g, theoretical yield from 1,2-dimethoxybenzene: 90.1%) (the method of Synthesis, 477, 1994).

Workup

  1. customdescribed in Synthesis, 477, 1994 and JP-A-8-119894
  2. customthe solution was reacted at 25° C. for 24 hours
  3. customAfter completion of the reaction
  4. filtrationthe precipitated crystal was collected by filtration
  5. washAfter the resultant crystal was washed with water (1 L)
  6. customdried

Sources & evidence

ORD record
ord-fb1c824139514220ae6415ee0d38c5f3
Source dataset
uspto-grants-2012_05
Patent number
US08178731B2

Reaction notes

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