Hydrochloric Acid → Trans-4-(2-chlorophenoxy)-1-ethyl-3-pyrrolidinol Hydrochloride

Participants

Reaction Steps

A mixture of 17.0 g. (0.15 mole) of 1-ethyl-3,4-epoxypyrrolidine, 20.5 g. (0.16 mole) of a o-chlorophenol and 3 drops concentrated hydrochloric acid was heated on a steam both overnight. The oil was dissolved in methylene chloride and washed with three 50-ml. portions of 5% sodium hydroxide and one 50-ml. portion of water. The methylene chloride solution was dried over anhydrous sodium sulfate, concentrated and chromatographed on silica gel to give 8.9 g. (25%) of an oil as residue. The oil was converted to the hydrochloride and recrystallized from ethyl acetateacetonitrile to yield white powder, m.p. 108°-110° C.

Provenance & Evidence