Abstract
Ethyl 4-vinyl-α-cyano-β-phenylcinnamate was prepared by a five step synthesis from 4-ethylbenzoic acid in an overall yield of 20%. The acid chloride of 4-ethylbenzoic acid was condensed with benzene to 4-ethylbenzophenone. The most critical step in the synthesis was the Knoevenagel condensation of 4-ethylbenzophenone with ethyl cyanoacetate which was accomplished with ammonium acetate as the catalyst. Ethyl 4-ethyl-α-cyano-β-phenylcinnamate was readily brominated with N-bromosuccinimide and the bromination product, ethyl 4-(1-bromoethyl)-α-cyano-β-phenylcinnamate was dehydrobrominated. Ethyl 4-vinyl-α-cyano-β-phenylcinnamate consists of a mixture of cis and trans isomers of nearly equal amounts as indicated in 1H nuclear magnetic resonance and 13C nuclear magnetic resonance spectroscopy. This new monomer was homopolymerized and copolymerized with styrene and methyl methacrylate with radical initiators.
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Sumida, Y., Vogl, O. Functional Polymers. VII. Ethyl 4-Vinyl-α-cyano-β-phenylcinnamate. Polym J 13, 521–536 (1981). https://doi.org/10.1295/polymj.13.521
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DOI: https://doi.org/10.1295/polymj.13.521