Reaction SMILES: [CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10]>O.C(Cl)(Cl)Cl>[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
Reactant: COc1ccccc1OC
Solvent: O
Solvent: ClC(Cl)Cl
Product: COc1cc2c3cc(OC)c(OC)cc3c3cc(OC)c(OC)cc3c2cc1OC
Temperature: 75 °C
Reaction time: 0.08 h

Procedure:
1,2-Dimethoxybenzene (138.0 grams, 0.999 mole) and ferric chloride (81.2 grams, 0.501 mole) were added to a glass resin kettle reactor and stirred under a nitrogen atmosphere as a slurry. The slurry exotherms to a 70° C. temperature, then after stirring for 10 minutes, the temperature of the slurry was 65° C. After an additional 5 minutes, the temperature of the slurry was 55° C. and at this time, deionized water (9.0 grams, 0.5 mole) was added dropwise to the slurry over a 5 minute period. At the completion of the water addition, the reaction temperature was increased to 75° C. and held therein for the next 20 minutes. The resultant slurry was diluted with deionized water (250 milliliters) then filtered. The precipitate was recovered and was washed with ethanol (400 milliliters) followed by filtration. The precipitate was recovered and washed with 5N aqueous hydrochloric acid (400 milliliters) followed by filtration. The precipitate was recovered and washed with deionized water (400 milliters) followed by filtration. The precipitate was recovered and dried in a forced air, convection type oven for 16 hours at 50° C. to provide a dry purple colored powder. Portions of the powder were dissolved in chloroform then applied to a silca gel column and eluted with chloroform. A yellow colored product band elutes first and was retained, while a purple colored band was left on the column. The chloroform solvent was removed from the eluted solution of product by rotary evaporation to provide a pale creme colored powder. After drying to a constant weight, 7.53 grams of product was recovered. High pressure liquid chromatographic analysis reveals a single peak for the 2,3,6,7,10,11-hexamethoxytriphenylene product in excess of 95 area percent (detector at 254 nm), with a single minor coproduct peak present. Differential scanning calorimetry of a portion (10.1 or 12.3 milligrams) of the product using a heating rate of 10° C. per minute, and a range from 30° to 350° C. under a stream of nitrogen flowing at a rate of 35 cubic centimeters per minute reveals a sharp melting point endotherm with a minimum at 311° C. and an enthalpy of 136 joules per gram (data averaged from two analysis). Fourier transform infrared spectrophotometric analysis of a potassium bromide pellet of the product reveals the presence of the C--H stretch vibration for the aromatic ring at 3104 cm-1, the C--H stretch vibration for the methoxy group at 2831 cm-1, the C--H stretch vibrations for the aromatic ring C=C groups at 1623, 1523 and 1463 (1437 shoulder) cm-1, the aromatic ring C--O vibration for the ether linkage at 1264 cm-1, the aliphatic portion of the C--O vibration for the ether linkage at 1045 cm-1, aromatic ring C--O stretch vibration at 1158 cm-1 and the C--H out-of-plane vibration for the aromatic rings at 832 and 779 cm-1.