Date of Publication

6-1-1969

Document Type

Thesis

Degree Name

Master of Science (M.S.) in Chemistry

Department

Chemistry

Language

English

Subjects

Naphthol, Paraconic acids, Isocrotonic acids

DOI

10.15760/etd.424

Physical Description

1 online resource (ii, 37 leaves)

Abstract

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-l-naphthol.

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Comments

Portland State University. Dept. of Chemistry

Persistent Identifier

http://archives.pdx.edu/ds/psu/9219

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