2,3,6,7,10,11-HEXAHYDROXYTRIPHENYLENE

Light brown to brown powder

The preparation of compound 4 is similar to that reported in the literature[14]. Hexamethoxytriphenylene (7 g, 17.14 mmol) was dissolved in dichoromethane (50 ml) and the solution thus obtained was cooled in ice bath. A solution of boron tribromide (11.47 ml) was then added slowly to the reaction mixture over a period of 30 min. After complete addition, the reaction was left stirring overnight in room temperature.The reaction mixture was then slowly poured into crushed ice(100 g) and the obtained mixture was stirred vigorously until the ice melted. It was then extracted with ethyl acetate (6 × 150 ml), dried over anhydrous sodium sulphate and evaporated to dryness giving dark purple solid. The yield was quantitative and this compound was used without further purification.EXAMPLE 6 2, 3, 6, 7, 10, 11-Hexamethoxytriphenylene (5.0 g, 12.2 mmol) was dissolved in 80 mL of dichloromethane under nitrogen and the reaction mixture was cooled to -70 °C. A solution of BBr34.2 g of ammonium persulfate (0.15 mol) was added to 16.5 g of catechol (0.15 mol) dispersed in 50 ml of a 70 wtpercent aqueous solution of sulfuric acid. The mixture was stirred for 7 hours at room temperature, and the resultant precipitate was then filtered and washed with water. 300 ml of acetone and 1.5 g of activated carbon were added to the precipitate, the mixture was stirred for 30 min at room temperature, and insoluble matter was subsequently filtered off from the mixture. 300 ml of ion- exchanged water was added to the filtrate, and then acetone was distilled off at distillation temperatures of 56 to 100°C under normal pressure (101.3 kPa). The resultant precipitate was filtered and dried under reduced pressure to afford 14.2 g of crystals of HHTP (yield: 83.1percent; purity > 99percent).Reaction and post-treatment were carried out in a similar manner to that in Example 1, except for using 68.4 g of ammonium persulfate (0.30 mol) and 250 ml of a 60 wtpercent aqueous solution of perchloric acid, thereby yielding crystals of HHTP (yield: 72.6percent; purity > 99percent).Catechol (22.0 g, 0.2 moles) and diiron trioxide (ferric oxide) (31.9 g, 0.2 moles) were added into water (110 mL), and 98percent sulfuric acid (440 g, 4.4 moles) was added dropwise to the solution while temperature of the solution was maintained at 30°C or lower, to adjust the concentration in percent by weight of sulfuric acid in the reaction system at 80percent. The solution was reacted at 30°C for 6 hours with stirring. After completion of the reaction, water (500 mL) was added dropwise to the reaction solution, and the reaction solution was stirred for another 30 minutes. The resultant precipitate was collected by filtration, and the obtained crude crystal was washed with water and dried to give crude crystal (19.2 g). After a part of the crude crystal (5.0 g among 19.2 g) was dispersed in a mixed solvent of water (50 mL) and acetonitrile (200 mL), the dispersion liquid was heated up and stirred for 1 hour. After that, this dispersion liquid was filtered in hot state to filter off insoluble matter, the filtrate was then concentrated under reduced pressure, and the precipitated crystal was collected by filtration, and then dried, to give 2, 3, 6, 7, 10, 11-hexahydroxytriphenylene (2.56 g, theoretical yield from catechol: 45.5percent) in black powder form.In a 100 ml double-necked flask,

Molecular Weight:324.3
XLogP3:2.7
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:6
Exact Mass:324.06338810
Monoisotopic Mass:324.06338810
Topological Polar Surface Area:121
Heavy Atom Count:24
Complexity:364
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes