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Synthesis of Caffeic Acid Derivatives via Dicyclohexylcarbodiimide
Coupling Reaction
Woong Chee Hao
Dr. Asnuzilawati Binti Asari
Chemical Sciences
University Malaysia Terengganu
Caffeic acid derivatives have demonstrated many biological and pharmacological
actions such as antioxidant, anti-inflammatory, anticancer, and antibacterial. The aim
of this research is to synthesize (E)-pentyl 3-(4-hydroxy-3-methoxyphenyl)acrylate. In
this study, caffeic acid and 1-pentanol was reacted by employing
Dicyclohexylcarbodiimide (DCC) coupling reaction in the presence of 4-
Dimethylaminopyridine (DMAP) as catalyst. From the IR spectrum obtained, the
product exhibited a sharp medium band at 1718 cm -1 confirming the presence ester
carbonyl group. The characteristic signal from
1 H NMR spectrum was observed at δ
4.14 assignable to methylene protons (-COO-CH 2 ) of ester. Unfortunately, the
percentage yield of the product was extremely low (7.43 %) and a lot of impurities
were emerged in the product. In conclusion, pure ester product was not successfully
obtained due to the presence of dicyclohexylurea (DCU) by-product. Changing the
condition or solvent used in this reaction was suggested in order to improve the
percentage yield of the product.
465 | U M T U N D E R G R A D U A T E R E S E A R C H D A Y 2018