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Date of Award
Master of Arts (M.A.)
Emerson G. Cobb
The synthesis of a keto-aldehyde from salicylaldehyde and benzaldehyde was attempted. The first step was to protect the carbonyl with a non-reactive group.
The bisulfite addition product and the 2,4-dinitrophenylhydrazone of salicylaldehyde were prepared. The methyl acetal, the sodium bisulfite addition product, and the 2,4-dinitrophenylhydrazone of benzaldehyde were also prepared.
The bisulfite addition of both aldehydes was found to be too unstable in the presence of aldehyde was recovered in each case. The methyl acetyl chloride also decomposed. This necessitated finding a more stable group to protect the aldehyde.
The 2,4-dinitrophenylhydrazone was unaffected by treatment with anhydrous aluminum chloride in both acetyl chloride and acetic anhydride. Other reactions have shown that a nitro group deactivates the benzene ring. This may be an explanation of the failure to get a Fries rearrangement or Friedel-Crafts addition.
This synthesis was not accomplished by this method, but considerable information was gained for use in further work.
Gakle, Paul Spencer. (1951). Intermediate compounds in the synthesis of lignin. University of the Pacific, Thesis. https://scholarlycommons.pacific.edu/uop_etds/1170