CHED 473 |
| The compound 2,6-dimethyl-4-m-methylphenyl-3-cyclohexenecarboxylic acid was made through a five-step synthesis. Acetaldehyde and ethyl acetoacetate were condensed by the Knoevenagel reaction in the presence of piperidine. It gave a bis ester, which was cyclized, hydrolyzed and decarboxylated to ethyl 2,6-dimethyl-4-oxo-2-cyclohexenecarboxylate (1). (1) was catalytically hydrogenated over platinum catalyst in alcohol to give ethyl 2,6-dimethyl-4-oxo-cyclohexanecarboxylate (2). Basic hydrolysis of (2) with KOH/EtOH/H2O afforded 2,6-dimethyl-4-oxocyclohexanecarboxylic acid (3). Grignard reaction of (3) with m-bromotoluene provided the title compound after dehydration. The final product will be characterized by X-ray single crystal analysis. We want to use the X-ray structure to study the interaction of the two enantiomers in the solid state. |
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Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster
Division of Chemical Education |