Hydrogen Bromide → 4-(4-[1,2,3]Triazol-1-yl-butyl)phenol

Participants

Reaction Conditions

Reaction Steps

1-[4-(4-Methoxyphenyl)butan-1-yl]-1H-1,2,3-triazole methanesulfonate (4.0 g, 12.22 mmol) was added to 48% hydrobromic acid (8 ml) and the mixture was heated at 80-90° C. for 6 hours. The mixture was ice-cooled, and after dropwise addition of 4N-sodium hydroxide (32 ml), washed with toluene. 6N Hydrochloric acid was added to the aqueous layer to make pH 6.3. The mixture was extracted with ethyl acetate (30 ml) and tetrahydrofuran (15 ml) and washed with water. Active charcoal (200 mg) was added, and the mixture was stirred at room temperature for 10 min. The mixture was filtrated and concentrated under reduced pressure. Ethyl acetate (10 ml) was added to the residue, and the mixture was refluxed. The mixture was allowed to cool and stirred for 30 min, and hexane (10 ml) was added. The mixture was stirred at room temperature for 30 min. The precipitated crystals were collected by filtration and dried under reduced pressure to give 4-[4-(1H-1,2,3-triazol-1-yl)butyl]phenol (2.25 g, yield 85%).

Provenance & Evidence