Synthesis of A Series of Clofibrate Drugs

A. Ashnagar¹*, N. Gharib Naseri² and KH. Parvizi Eghlimi¹

¹School of Pharmacy, Ahwaz Jundi Shapour University of Medical Sciences, Ahwaz (Iran) ²Ahwaz Faculty of Petroleum Engineering, Petroleum University of Technology (Iran)

Clofibrate is a drug especially good at lowering triglycerides and very-low-density lipoprotein. It can help prevent cholesterol clogging blood vessels. It also lowers blood fats and cholesterol for patients who are at risk of getting heart disease or a stroke. It is only for patients whose cholesterol level is not controlled by diet. The main purpose of the present work, due to the therapeutic effects and also rather cheap and available starting materials, was to synthesize several homologs of clofibrate and establish and characterize the chemical structures of the intermediates and products by various spectroscopic techniques. Clofibrate is synthesized simply by condensation of p-chlorophenol with acetone and chloroform and the resultant acid [2-(4-Chlorophenoxy)-2-methylpropanoic acid] (I) was esterified with ethyl alcohol in the presence of catalytic amount of sulphuric acid to give clofibrate. Esterification of the acid (I) with various different alcohols (methanol, 1-propanol, 2-propanol and 1-butanol) resulted in the formation of different products (III-VI). Chemical structures of the products were carefully determined by their corresponding IR, HNMR and MS (EI) and by their boiling points.

Clofibrate drugs, Clofibrate, a-p-chlorophenoxyisobutyrate, ethyl 2-(4-chlorophenoxy)-2-methyl-propanoate.