CHED 1821 |
| Dioxins are some of the most toxic chemicals known to science. Diphenyl ethers are structural elements found in biological toxins in the environment such as dioxins as well as in medicinally useful antibiotics such as vacomycin. The purpose of this paper is to report the synthesis of diphenyl ether derivatives carried out by undergraduate science students majoring in forensic science and other science disciplines. The reported derivatives of diphenyl ethers serve as intermediates in the synthesis of these biologically active molecules. A retrosynthetic analysis approach was employed to prepare 4-methyl-4'-nitrodiphenyl ether via an Ullmann coupling reaction using p-cresol and p-chloronitrobenzene as synthons. Regioselective chlorosulfonation at the the 2-position at 0¢ªC followed by reaction with 1-hexanol produced the corresponding sulfonic ester derivative which was the oxidized with KMnO4 in the presence of pyridine as a solvent to produce the 4-carboxylic acid derivative of diphenyl ether as the desired product. |
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General Papers
1:00 PM-4:50 PM, Thursday, March 29, 2007 McCormick Place North -- Room N230A, Level 2, Oral
Division of Chemical Education |