1,2-Dichloroethane → 1-(Dioctadecylamino)methyl-4-carbomethoxy benzene

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Reaction Steps

The nitrile (15 g.), ethylene dichoride (200 ml.), methanol (50 ml.) and water (20 ml.) are combined and stirred at room temperature. Hydrogen chloride gas is bubbled into the mixture for three hours after which the yellow solution is refluxed for three hours. Methanol (50 ml.) and water (10 ml.) are added and hydrogen chloride bubbled into the mixture for one hour and refluxing continued for 14 hours. Methanol (10 ml.) and water (2 ml.) are added and hydrogen chloride bubbled in for one hour. The mixture is refluxed for four hours, cooled to room temperature and made alkaline by addition of saturated aqueous sodium bicarbonate solution. The ethylene dichloride phase is separated and the aqueous phase extracted with chloroform (2× 100 ml.). The combined organic solutions are washed with water (100 ml.), dried (Na2SO4) and evaporated to give 1-(dioctadecylamino)methyl-4-carbomethoxy benzene (14.0 g., 73.6% yield).

Provenance & Evidence