Aliphatic Iodo Derivatives of Tetrahydrofuran Formation by Means of Titanic Heterogeneous Catalyst as By-Products at the Synthesis of 2-Arylpropanoic Acids from Acetophenone Derivatives

Josef Jampílek¹ (jamp@faf.cuni.cz), Martin Doležal¹, Jiří Kuneš²

¹ Department of Pharmaceutical Chemistry and Drug Control, ² Department of Inorganic and Organic Chemistry, Charles University in Prague, Faculty of Pharmacy in Hradec Králové, Czech Republic.

Summary

This paper describes formation of 4-iodobutan-1-ol and 4-iodobutyl acetate as by-products of the synthesis of 2-arylpropanoic acid in THF, using TiI₄ as the heterogeneous catalyst and LiAlH₄, CFCl₃. These aliphatic iodo derivatives of THF are formed by means of THF cleaving, which has been used as a solvent. The first derivative is generated by opening THF ring in acid environment in 68 % yield. The mechanism of 4-iodobutyl acetate formation (in 8 % yield) may be a combination of opening THF ring and a rearrangement by means of unreacted TiI₄ as the Lewis acid.