4-Chlorophenol → Methyl(p-chlorophenoxy)[p-(p-chlorophenoxy)phenyl]acetate

Participants

Reaction Steps

To a solution of 1.19 g of sodium methoxide in 40 ml of methanol is added 3.21 g of 4-chlorophenol. A few crystals of potassium iodide are added, followed by a solution of 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of benzene. The solution is heated at reflux overnight. After cooling to room temperature, the solution is poured into 100 ml of water and extracted with two 100 ml portions of ether. The combined extracts are washed with 50 ml of 5% NaOH, 50 ml of saturated brine and dried over MgSO4. The solvent is evaporated at reduced pressure and the residue is triturated with petroleum ether to give the product as white crystals, mp 100°-101.5° C.

Provenance & Evidence