Synthesis of new optically active α-alkoxypropionanilides

Two promising routes towards synthesis of the hitherto unknown α-alkoxypropionanilides were explored with success. As expected, facile displacement of the bromide in l(?)α-bromopropionanilide by alkoxide lead to inversion of configuration with considerable racemization, whereas substitution of the chloride in l(?) α-alkoxypropionyl chloride by arylamine proceeded with little or no racemization. α-Ethoxypropionanilide and the higher alkoxy homologues appear as low-melting noncrystallizable gum. Optical properties and other physical data for few model compounds of this new anilide series are reported.