Portland State University. Department of Chemistry
Philip C. Roberti
Term of Graduation
Date of Publication
Master of Science (M.S.) in Chemistry
Naphthol, Paraconic acids, Isocrotonic acids
1 online resource (ii, 37 pages)
The γ-o-substituted-phenylparaconic acids were prepared by a method patterned after that of Fuson. These paraconic acids were prepared in good yield. A re-investigation of the Perkin and Fittig methods of preparing γ-phenylisocrotonic acid was carried out without success.
The synthesis of γ-o-halophenylisocrotonic acids by thermal, and catalyzed decarboxylation of γ-o-halophenylparaconic acid, have been carried out in good yield. An effective catalyst, optimum temperature and reaction period of decarboxylation of the γ-o-halophenylparaconic acids have been determined. Infrared absorptions have characterized the γ-o-halophenylisocrotonic acids formed to be in the stable trans form.
Cyclization of γ-o-halophenylisocrotonic acids was accomplished by isomerization of the trans acid to cis acid by ultra-violet irradiation, followed by refluxing in the presence of sodium acetate and acetic anhydride. The subsequent hydrolysis of the acetylatednaphthol afforded the 5-halo-1-naphthol.
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Chow, Clark Keelock, "Cyclization Studies Involving the Synthesis of 5-Substituted-1-Naphthol" (1969). Dissertations and Theses. Paper 424.