4-Chlorophenol → HCID 131711327, compound

Participants

Reaction Steps

A mixture of 1.55 g of p-chlorophenol, 0.47 g of 60% sodium hydride-oil dispersion and 20 ml of tetrahydrofuran is stirred at room temperature for 90 minutes. To the mixture is added 2.22 g of potassium iodide, 1 ml of hexamethylphosphoramide and dropwise 5.04 g of methyl bromo{p-[2-(p-tert.-butylphenoxy)ethoxy]phenyl}acetate in 30 ml of tetrahydrofuran. The mixture is refluxed for 18 hours and poured into 350 ml of ice-water containing 1 ml of acetic acid. After stirring in an ice bath for 30 minutes, the mixture is filtered and the solid washed with water to give 5.5 g of product as tan crystals. Recrystallization by dissolving in acetone, adding hexane and distilling off the acetone gives 3.9 g of white crystals, mp 128°-130° C.

Provenance & Evidence