Physical Sciences and Mathematics Commons^™

Intermediate Compounds In The Synthesis Of Lignin, Paul Spencer Gakle

University of the Pacific Theses and Dissertations

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 …