Potassium Iodide → Methyl alpha-(2-naphthyloxy)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Participants

Reaction Steps

To a solution of 3.60 g of 2-naphthol, 1.19 g of sodium methoxide and 50 mg of potassium iodide is added 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of benzene. The solution is maintained at reflux overnight and then poured into 100 ml of water. The mixture is then extracted with 2 × 75 ml of ether and the combined extracts are washed with 2 × 50 ml of 5% NaOH, 50 ml of water, 50 ml of saturated brine and dried (MgSO4). Evaporation of the solvent yields a yellow oil. Chromatography on 100 g of silica gel (benzene, 400 ml) yields a green glass. Further elution with 200 ml of benzene yields the product as a glass.

Provenance & Evidence