Solvent-Free Conversion of alpha-Naphthaldehyde to 1-Naphthoic Acid and 1-Naphthalenemethanol: Application of the Cannizzaro Reaction

Solvent-Free Conversion of alpha-Naphthaldehyde to 1-Naphthoic Acid and 1-Naphthalenemethanol: Application of the Cannizzaro Reaction

The Cannizzaro reaction is routinely covered in organic textbooks, but owing to the shortage of suitable procedures for the undergraduate teaching laboratory, this reaction is seldom performed in a first-year organic chemistry class. In this experiment, powdered potassium hydroxide and α-naphthaldeh...

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Veröffentlicht in:Journal of chemical education 2004-12, Vol.81 (12), p.1794
Hauptverfasser: Esteb, John J, Gligorich, Keith M, O'Reilly, Stacy A, Richter, Jeremy M
Format: Artikel
Sprache:eng
Schlagworte:
Acids
Analytical chemistry
Chemistry
Design of experiments
Hazardous Materials
Laboratory Experiments
Potassium
Potassium hydroxides
Science Education
Science Experiments
Solvents
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Zusammenfassung:The Cannizzaro reaction is routinely covered in organic textbooks, but owing to the shortage of suitable procedures for the undergraduate teaching laboratory, this reaction is seldom performed in a first-year organic chemistry class. In this experiment, powdered potassium hydroxide and α-naphthaldehyde are heated under solvent-free conditions to produce 1-naphthoic acid and 1-naphthalenemethanol in 86% and 79% yields, respectively. The solvent-free nature of this procedure greatly reduces the quantity of waste generated by students relative to the typical solvent-based method of preparation.
ISSN:0021-9584
1938-1328
DOI:10.1021/ed081p1794