4-Iodophenol → 1-Iodo-4-propoxybenzene

Participants

Reaction Steps

A mixture of 4-iodophenol (6.6 g), 1-iodopropane (5.1 g), anhydrous potassium carbonate (13.8 g) and acetone (100 ml) was stirred at reflux for 6 hours. Two further portions of 1-iodopropane were added after one hour (5.1 g) and two hours (5.1 g). The acetone was removed by evaporation, the residue was treated with water (100 ml) and the mixture extracted with dichloromethane (2×30 ml). The organic extracts were combined, dried (MgSO4) and evaporated. The residue, an oil, was distilled at 150° C. and 0.5 mm pressure (using a Kugelrohr oven) to give 4-n-propoxyiodobenzene as a colourless oil (7.2 g), NMR(CDCl3): 0.9-1.08(3H,t), 1.7-1.9(2H,m), 3.82-3.92(2H,t), 6.62-6.72(2H,d), 7.5-7.6(2H,d); m/z 262 (M).

Provenance & Evidence