4-Chloro-3-methylphenol → Methyl (4-chloro-3-methylphenoxy)[p-(p-chlorophenoxy)phenyl]acetate

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Reaction Steps

To a solution of 3.565 g of 4-chloro-3-methylphenol, 1.188 g of sodium methoxide and 50 mg of potassium iodide in 40 ml of methanol is added 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of benzene. The mixture is refluxed overnight and poured into 100 ml of water. The mixture is extracted with `× 75 ml of ether and the combined extracts are washed with 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 yields a colorless oil.

Provenance & Evidence