Sodium Iodide → HCID 14349148, compound

Participants

Reaction Steps

A mixture of 2-chloromethyl pyrrole (5.8 g, 0.05 mol), 1-(4-hydroxyphenyl)-1-hexanol (9.75 g, 0.05 mol), finely powdered anhydrous potassium carbonate (7 g, 0.05 mol) and sodium iodide (0.75 g, 0.005 mol) in anhydrous acetone (125 ml) were refluxed for 6 hours. The reaction mixture was filtered, and the residue was washed with acetone (25 ml). The filtrate was concentrated at the rotary evaporator to about 25-30 ml and the dark liquid was taken up in ethyl acetate (100 ml). The organic extract was washed with 5% sodium hydroxide solution, water and brine, and then dried over MgSO4. All volatiles were removed, and the dark oil was chromatographed on silica gel (15% ethyl acetate in hexanes) to leave the desired product as a light yellow liquid (4.1 g, 30%).

Provenance & Evidence