4-Chloro-3-methylphenol → 4-Chloro-1-(4-chloro-3-methylphenoxy)-2-butanol

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To a mixture of 286 g (2 mole) of 3-methyl-4-chlorophenol, 700 ml of tertiary butanol, 700 ml of water and 3.0 mole of 1,4-dichloro-2-butanol, sodium hydroxide (2.9 moles, 230 g in 700 ml of water) was added with stirring at 40° C. to maintain a pH of 9.5-10.0 as the reaction progressed. The addition was 10 hr; the reaction was stirred at 40° C. for 48 hr. The resulting reaction mixture was extracted with chloroform sodium hydroxide at 25° C. The chloroform extract was washed with sodium sulfate. The dried chloroform solution was concentrated and the residue was distilled under reduced pressure to give 110.9 g of the product which distilled at 135°-143° C./0.007 mm and melted at 87°-89° C. after recrystallization with isopropanol and petroleum ether (30°-60° C.).

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