Acetic Acid → 2-(1H-Pyrrol-1-Yl)Phenol

Participants

Reaction Steps

A mixture of 2,5-dimethoxytetrahydrofuran (39.6 g), o-aminophenol (36 g), dioxane (300 ml), and glacial acetic acid (180 ml) are heated under reflux for 4 hr. The solvents are removed and the residue distributed between ethyl acetate and 5% NaHCO3. The organic phase is washed with water, dried (MgSO4), filtered, and evaporated. The dark oily residue is subjected to chromatography on 2 kg of silica and eluted with chloroform to afford an oil. After being covered with hexane and stored for several days, the oil solidifies giving the title compound, m.p. 52° - 54° C. (Reported m.p. by Artico, et al., cited above, 45° - 47° C).

Provenance & Evidence