Potassium Iodide → Methyl alpha-[p-(Benzyloxy)phenoxy]-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Participants

Reaction Steps

To a solution of 5.0 g of p-benzyloxyphenol and 1.19 g of sodium methoxide in 40 ml of methanol is added 50 mg of potassium iodide and 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of benzene. The mixture is refluxed for 22 hours and poured into ice and water. The mixture is extracted with ether and the ether extracts washed with 10% potassium carbonate and with water. The extracts are dried (MgSO4) and the solvent removed under vacuum to give an oily solid. Trituration with hexane plus a small amount of acetone and chilling gives crystals. Filtration gives the product as off-white crystals, mp 91°-96° C. Recrystallization by dissolving in hot acetone, diluting with petroleum ether, chilling and filtering gives the product as white crystals, mp 88°-90° C.

Provenance & Evidence