Date of Award
Union College Only
Bachelor of Science
The synthesis of phenyl carbamate from urea, phenol, and Lewis acid was attempted with varied results being observed. The proposed reaction mechanism involves and Acyl-2 type reaction with a nucleophilic attack on urea by phenol. The Lewis acid is present to add carbocation character to the urea and to further complex with by-products, thus driving the reaction to completion. The solvents utilized were isopropyl alcohol, dichloromethane, and tetrahydrofuran. The reaction parameters were varied in an effort to successfully run a reaction mechanism. Phenyl carbamate was not isolated and what was observed of the reactions did not appear to follow the proposed mechanism. A white crystalline product was isolated and found to have both amide and aromatic character, but its identity remains unknown.
Barrett, Michael W., "The synthesis of phenyl carbamate (from urea, phenol, and a Lewis acid)" (1986). Honors Theses. 2003.