Title of project
Green Synthesis of d,l-Phenylalanine using 2-Methylhydrofuron
Faculty Advisor
James Wollack, Alexandra Jones
Department
Chemistry
Green Synthesis of d,l-Phenylalanine using 2-Methylhydrofuron
Abstract: Green Synthesis of d,l-Phenylalanine using 2-Methyltetrahdrofuron
Johnay Fanning, Nicole Blanshan, Rachel Scherrer
Phenylalanine is an amino acid with many uses. The two forms, d, and l interact differently with chiral enzymes. The d form is found in compounds such as aspirin and salicylic acid, and is used to combat pain. The l form is used as a stimulant, appetite suppressant, and mood enhancer. Interestingly, the two forms together are used by the brain to produce norepinephrine, an important neurotransmitter. It also helps to replace dopamine. This three step synthesis started with the saponification of diethyl benzylmalonate to create benzylmalonic acid. This was then converted to bromobenzylmalonic acid via an SN2 reaction. This second step was also attempted using a greener solvent by changing from diethyl ether to 2-methyltetrahydrofuron. Finally, the bromobenzylmalonic acid was decarboxylated to produce the final product phenylalanine.