Lei Ni
2004
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Journal
Journal of Shenyang Institute of Chemical Technology
Abstract
2-(N,N-biscarboxymethyl)aminomethyl-6-benzoyl-4-methylphenol was synthesized from 4-methylphenol through a sequence of reaction, esterfication by benzoyl chloride, Fries rearrangement catalyzed by AlCl_3 without any solvent, chloromethylation by formaldehyde and concentrated HCl, amination by diethyl iminodiacetate using TEA as a proton absorbent, hydrolysis by Ba(OH)_2 solution. The reaction conditions involved in the synthetic route were studied and the structure of the title compound was characterized by elemental analysis, IR, HNMR, Raman and MS. The reaction of Fries rearrangement and amination was studied. The results show that this method has advantages of good yield and simple operation.