Date of Award
College of Science, Engineering, and Technology (COSET)
MS in Chemistry
Professor John B Sapp
The Fries rearrangement was first done by treating phenyl acetate with Aluminum chloride and heat. Aluminum chloride is a Lewis acid and work well under the prescribed conditions. This study uses a different Lewis acid, Trifluroacetic acid. (TFA) in a similar rearrangement but uses 2-naphthol as the substrate. The results show TFA as an effective reagent to cause the rearrangement ofAcetyl, propionyl and phenyl esters of2-Naphthol. The infrared spectrum of the starting ester showed no evidence of the hydroxyl functional ' group while the infrared spectrum of the product showed positive evidence of the presence of the hydroxyl functional group, as it should, when the rearrangement occurred. Structures of the resulting hydroxyl ketones were determined and confirmed using Infrared and Nuclear Magnetic spectroscopy.
Gbenda., Tamba R., "Use of Trifluroacetic Acid in the Fries Rearrangement" (2014). Theses (Pre-2016). 12.