Sodium borohydride → Ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]-2-methylpropionate hydrochloride

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Reaction Steps

In 40 ml of methanol is dissolved 5.3 g of ethyl 2-[4-{N-(4-chlorophenyl)formimidoyl}phenoxy]-2-methylpropionate. Over a period of about 1 hour, 0.58 g of sodium borohydride is added to the solution at 20° to 25° C. with stirring. After stirring the mixture at room temperature for 1 hour, the methanol is distilled off, and the residual oil is dissolved in ether. The solution is washed with water and dried, and the ether is thereafter distilled off. The resulting oily residue (4.2 g) is dissolved in 20 ml of ether. A mixture of hydrochloric acid and ethanol is added to the solution. The resulting precipitate is collected by filtration and washed with ether to give 3.9 g of ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]-2-methylpropionate hydrochloride, mp 139° to 141° C. Recrystallization of the crystals from a mixture of methanol and ether gives 3.1 g of crystals, mp 143° to 145° C. The crystals are suspended in a mixture of ether and water, and the suspension is adjusted to pH 8 to 9 by addition of 28% ammonia water. The ether layer is thereafter separated, washed with water and dried. After drying, removal of the ether by distillation gives 2.9 g of ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]-2-methylpropionate as an oil.

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