Potassium Iodide → 1-[4-(4-methoxyphenyl)butan-1-yl]-1H-1,2,3-triazole methanesulfonate

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Reaction Steps

1-(4-Chlorobutyl)-4-methoxybenzene (950 mg, 4.78 mmol), 1H-1,2,3-triazole (660 mg, 9.55 mmol) and potassium iodide (793 mg, 4.78 mmol) were added to t-butanol (5 ml). Sodium hydroxide (382 mg, 9.55 mmol) was added and the mixture was refluxed under heating for 11 hours. After cooling to room temperature, toluene and water were added and the mixture was partitioned. The organic layer was washed successively with water, 20% citric acid, saturated aqueous sodium hydrogen carbonate and water, and was concentrated under reduced pressure. To the residue were added ethyl acetate (6 ml) and isopropyl ether (3 ml). Methanesulfonic acid (402 mg, 4.18 mmol) was added at room temperature. Ethyl acetate/isopropyl ether=2/1 (2 ml) was added and the mixture was stirred at room temperature for 30 min. The precipitated crystals were collected by filtration and dried under reduced pressure to give 1-[4-(4-methoxyphenyl)-butan-1-yl]-1H-1,2,3-triazole methanesulfonate (1.14 g, yield 73%).

Provenance & Evidence