Novel Synthesis of Styryl Ethers

Katherine Davis, Chemistry (2nd from left in photo)

Faculty Mentor:  Dr. David Hunt

           I am researching a novel synthetic method for forming styryl ethers, key intermediates in the synthesis of biologically active compounds.  The goals of this research are to discover a method which involves a minimal number of steps while producing the desired product in high yield.  Throughout the program, I tested and perfected a procedure that was proven to form a substituted aryl acetaldehyde, which would then be converted to a styryl ether.  I have made significant progress with this project as a whole.  The complete process of converting each starting material to a pure styryl ether includes a series of five reactions.  The first step converts an aryl ketone to a glycidic ester via a Darzen’s condensation.

           The ester is then hydrolyzed to form a carboxylate salt which, upon acidification, provides the aldehyde. 

           The aldehyde reacts with methanol and an acid catalyst to form an acetal.  From seven ketone starting materials, I have successfully created five acetals, which, when heated, will eliminate methanol to provide the desired styryl ether.

Personal Statement

              Participating in the Summer Undergraduate Research Program at TCNJ has been both enjoyable and meaningful.  I decided to apply for the program in order to gain lab experience and to help me evaluate my options for after graduation.  The research program has introduced me to the type of work I may encounter working in a professional research lab.  It has given me experience with various lab procedures, and it has helped perfect my laboratory techniques.  Also, taking part in this program has made me more independent in my work and skilled at solving problems and determining improvements based on my results.  This program has brought me closer with professionals in the chemistry department along with other students.  I have decided to continue doing research during the academic year with my faculty advisor, and working with upperclassmen has helped me strive to advance my skills.  Aside from the interdepartmental closeness that comes with working in a research lab, the weekly SURP events helped the entire group of students and faculty share progress and experiences gained from this program.