UBC Theses and Dissertations

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UBC Theses and Dissertations

The polymerization and synthesis of phenyl vinyl ether and certain derivatives (part 1), and the synthesis of Schiff's bases from 2- aminovanillin (part 2) Harris, Gordon Richard


Certain aromatically substituted phenyl vinyl ethers were prepared by means of a two-step synthesis involving first, the synthesis of the corresponding beta-chlorophenetole derivative and subsequently treating this compound with flake potassium hydroxide to yield the vinyl ether. The beta-chlorophenetole derivatives prepared were: ortho-methyl-, meta-methyl-, para-methyl-, ortho-methoxy-, para-methoxy-, ortho-chloro-, and ortho-phenyl-beta-chlorophenetole. The vinyl ethers prepared were: phenyl, ortho-methyl-, meta-methyl-, and para-methyl-phenyl vinyl ether. Allyl phenyl ether was also prepared. The polymeric properties of these ethers were investigated. 2-aminovanillin was prepared from vanillin and its condensations with anthranilic acid, ortho-toluidine, ortho-phenylenediamine, and ortho-aminophenol were attempted. Diagnostic derivatives of 2-aminovanillin were also prepared: 2-acetaminovanillin, 2-aminovanillin phenylhydrazone, 2-aminovanillin 2,4-dinitrophenylhydrazone.

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