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

HRID 2425742Notes

Reaction equation

HRID 2425742 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-e5838ccfc23044a2984831f8362c3628
Source dataset
uspto-grants-2011_06
Patent number
US07964757B2

Reaction notes

Loading…