It was decided in this problem to prepare 2-phenyl-2,1,3-triazole-4-carboxaldehyde (III) as a starting material by the method suggested by Hann and Hudson and run a number of typical aldehyde reactions with it. The preparation of (III) involved: (1) The hydrolysis of sucrose to form glucose and fructose; (2) conversion of these two sugars to D-glucose phenylosazone (I), by reaction with phenylhydrazine; (3) transformation of (I) to D-glucose phenylosotraizole (II), by the action of hot aqueous copper sulfate; and (4) oxidation of the side chain from (II) with sodium periodate, forming (III).
The reactions selected were: (1) the Grignard reaction; (2) the Perkin reaction; (3) condensation of the aldehyde with a diamine to yield an imidazolidine; (4) oxidation to the acid and condensation of this acid with a diamine to yield an imidazoline; (5) condensation with acetone; and (6) a crossed Cannizzaro reaction, yielding primarily 2-phenyl-2,1,3-triazol-4-yl-carbinol.
Lilly Research Laboratories
Level of Degree
Department of Chemistry and Chemical Biology
First Committee Member (Chair)
Jesse LeRoy Riebsomer
Second Committee Member
John Francis Suttle
Third Committee Member
William Jacob Koster
Sumrell, Gene. "Synthesis of 2-Phenyl-2,1,3-Triazole-4-Carboxaldehyde and Some Derivatives." (1948). https://digitalrepository.unm.edu/chem_etds/83