Pyrogallol → 2-Ethoxy-benzo[1,3]dioxol-4-ol

Participants

Reaction Steps

Pyrogallol (0.50 g, 3.96 mmol), triethyl orthoformate (0.80 cm3, 4.81 mmol) and amberlyst-IR-120(plus), (0.11 g, 5% weight alcohol) were combined in dried toluene (40 cm3) and heated to reflux under nitrogen for 28 hours. Any low boiling solvents were removed by distillation through a 10 cm Vigreux column, and the reaction vessel was recharged with toluene as required. The cooled solution was filtered through a pad of celite, and the filtrate was evaporated under reduced pressure. The residue was filtered through a pad of silica with ethyl acetate (20% in heptane), and the filtrate was evaporated under reduced pressure to give the protected pyrogallol, (0.67 g, 92%) as clear oil.

Provenance & Evidence