Hydrogen iodide → 2,3,6,7,10,11-Hexahydroxytriphenylene hydrate

HRID 1925790Notes

Reaction equation

HRID 1925790 reaction equation
C[O:2][C:3]1[C:20]([O:21]C)=[CH:19][C:18]2[C:17]3[C:12](=[CH:13][C:14]([O:25]C)=[C:15]([O:23]C)[CH:16]=3)[C:11]3[C:6](=[CH:7][C:8]([O:29]C)=[C:9]([O:27]C)[CH:10]=3)[C:5]=2[CH:4]=1.I>C(O)(=O)C>[OH2:2].[OH:2][C:3]1[C:20]([OH:21])=[CH:19][C:18]2[C:17]3[C:12](=[CH:13][C:14]([OH:25])=[C:15]([OH:23])[CH:16]=3)[C:11]3[C:6](=[CH:7][C:8]([OH:29])=[C:9]([OH:27])[CH:10]=3)[C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 46073632,3,6,7,10,11-Hexamethoxytriphenylene

Product 1

HCID 569245442,3,6,7,10,11-Hexahydroxytriphenylene hydrateYield 171.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Subsequently, to the obtained 2,3,6,7,10,11-hexamethoxytriphenylene (28.2 g, 0.069 moles), 57% hydroiodic acid (235.3 g, 1.05 moles) and acetic acid (145 mL) were added, and the solution was refluxed for 2 hours. After completion of the reaction, the solution was cooled down to room temperature, and the precipitated crystal was collected by filtration. The crystal collected by filtration was dried under reduced pressure to give gray type B crystal of 2,3,6,7,10,11-hexahydroxytriphenylene monohydrate (20.2 g, yield: 85.5%) (the method of JP-A-8-119894). Also, the resultant gray compound was confirmed to be 2,3,6,7,10,11-hexahydroxytriphenylene monohydrate by 1H-NMR analysis and measurement of water content by Karl-Fischer measuring instrument. In addition, the measurement results of X-ray powder diffraction spectrum of the type B crystal are shown in FIG. 5 and also, main peak values of the type B crystal are shown in Table 3. Also, the measurement of X-ray powder diffraction spectrum was carried out in the same way as in Example 6.

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. customAfter completion of the reaction
  3. filtrationthe precipitated crystal was collected by filtration
  4. filtrationThe crystal collected by filtration
  5. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-2ad70ea441424b80aa04078af89089c2
Source dataset
uspto-grants-2012_05
Patent number
US08178731B2

Reaction notes

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