1,2-dihexoxybenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 750 mL of glacial acetic acid, 69.3 g (253 mmol) of iodine, 32.8 g (144 mmol) of periodic acid, 150 mL of distilled water, and 22.5 mL of concentrated sulfuric acid were added. The resulting mixture was stirred at ambient temperature for five minutes, and 80.00 g (287 mmol) of 1,2-dihexyloxybenzene was added. Then, the mixture was stirred at 40° C. for 24 hours. The obtained reaction mixture was cooled to ambient temperature, washed with a KOH aqueous solution (1 M, 1.5 L) and 3 L of distilled water, and extracted with 800 mL of chloroform. The organic phase was dried over MgSO4 and the solvent was evaporated. The residue was purified by column chromatography and was then distilled. As a result, 218.6 g of a light brown liquid was obtained. Then, the mixture was stirred at 40° C. for 24 hours The obtained reaction mixture was cooled to ambient temperature washed with a KOH aqueous solution (1 M, 1.5 L) and 3 L of distilled water extracted with 800 mL of chloroform The organic phase was dried over MgSO4 the solvent was evaporated The residue was purified by column chromatography was then distilled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 750 mL of glacial acetic acid, 69.3 g (253 mmol) of iodine, 32.8 g (144 mmol) of periodic acid, 150 mL of distilled water, and 22.5 mL of concentrated sulfuric acid were added. The resulting mixture was stirred at ambient temperature for five minutes, and 80.00 g (287 mmol) of 1,2-dihexyloxybenzene was added. Then, the mixture was stirred at 40° C. for 24 hours. The obtained reaction mixture was cooled to ambient temperature, washed with a KOH aqueous solution (1 M, 1.5 L) and 3 L of distilled water, and extracted with 800 mL of chloroform. The organic phase was dried over MgSO4 and the solvent was evaporated. The residue was purified by column chromatography and was then distilled. As a result, 218.6 g of a light brown liquid was obtained. Then, the mixture was stirred at 40° C. for 24 hours The obtained reaction mixture was cooled to ambient temperature washed with a KOH aqueous solution (1 M, 1.5 L) and 3 L of distilled water extracted with 800 mL of chloroform The organic phase was dried over MgSO4 the solvent was evaporated The residue was purified by column chromatography was then distilled

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,2-Dihexyloxybenzene (11.14 g; 40 mmol) and N-methylformanilide (5.41 g; 40 mmol) are cooled to 0° C., and phosphorus oxychloride (6.13 g; 40 mmol) is added. Heating is then carried out for 1 hour at 25° C., followed by stirring for 4 hours at 60° C. The reaction mixture is poured onto ice and then adjusted to pH 6. Extraction is carried out with tert-butyl methyl ether (2×200 ml), and washing is carried out with NaHCO3 (2×100 ml). The organic phase is dried over Na2SO4, filtered and concentrated to dryness by evaporation. Heating The reaction mixture is poured onto ice Extraction washing The organic phase is dried over Na2SO4 filtered concentrated to dryness by evaporation

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Pyrocatechol (55.1 g; 0.5 mol) is dissolved in DMF (400 ml), and K2CO3 (207.3 g) is added. The mixture is heated to 70° C. 1-Bromohexane (198 g; 1.2 mol) is then added dropwise, and heating is carried out for 15 hours at 80° C. Further DMF (400 ml) and water (1 liter) are subsequently added. Extraction is then carried out with tert-butyl methyl ether (2×500 ml), and the organic phase is washed with water (3×100 ml) and dried over Na2SO4. After filtration, concentration to dryness by evaporation is carried out. heating Extraction the organic phase is washed with water (3×100 ml) dried over Na2SO4 After filtration, concentration to dryness by evaporation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 69.3 g (253 mmol) of iodine, 32.8 g (144 mmol) of periodic acid, 150 mL of distilled water and 22.5 mL of concentrated sulfuric acid were added to 750 mL of glacial acetic acid and stirred for 5 minutes at room temperature followed by the addition of 80.00 g (287 mmol) of 1,2-dihexyloxybenzene and stirring for 24 hours at 40° C. The resulting reaction mixture was cooled to room temperature, washed with aqueous KOH solution (1 M, 1.5 L) and 3 L of distilled water, and then extracted with 800 mL of chloroform. The organic phase was dried with MgSO4 followed by distilling off the solvent. The residue was purified by column chromatography followed by distilling to obtain 218.6 g of a light brown liquid. stirring for 24 hours at 40° C The resulting reaction mixture was cooled to room temperature washed with aqueous KOH solution (1 M, 1.5 L) and 3 L of distilled water extracted with 800 mL of chloroform The organic phase was dried with MgSO4 by distilling off the solvent The residue was purified by column chromatography by distilling