The Synthesis of Chalcone Derivative Compounds from Benzaldehyde Derivatives in 1-Dodecyl-3-methylimidazolium bromide Ionic Liquid as Medium Utilizing MAOS (Microwave­ Assisted Organic Synthesis) Method

• Main Author: Febriana Santoso, Reneva
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/42125
• Institution: Institut Teknologi Bandung

Chalcone is one of ketone compounds that contains keto-ethylenic group (-CH=CH-CO-) and have been studied to have various biological activities, such as anti-inflammatory, anti­ microbial, anticancer, and anti-tumor. Chalcone can be synthesized by Claisen-Schmidt condensation from aromatic aldehyde and aromatic ketone. In this study, 3-(2-hydroxy-3- methoxy-phenyl)-1-phenyl-2-propenone (compound 1), 3-(2-hydroxy-phenyl)-1-phenyl-2- propenone (compound 2), and 3-(4-methoxy-phenyl)-1-phenyl-2-propenone (compound 3) have been successfully synthesized by utilizing MAOS (Microwave-Assisted Organic Synthesis) method in 1-dodecyl-3-methylimidazolium bromide ([DdMim]Br) ionic liquid medium as green-chemistry implementation. The compound 1 was obtained from the reaction between a-vanillin and acetophenone in 57,54% yields and melting point of 84-85 °C. Compound 2 was obtained from the reaction between salicylaldehyde and acetophenone in 52,64% yields and melting point of 154-155 oc. Compound 3 was obtained from the reaction between p-anisaldehyde and acetophenone in 7,06% yields with melting point of 74-75 °C, along with other side-products are 7-methoxyflavanone in I 0,17% yields and 3-hydroxy-3-(4-methoxy-phenyl)-1-phenylpropanone in 7,71% yields. The structure of the synthesized chalcones has been confirmed using FTIR and NMR spectroscopy. A typical spectrum of those chalcones featured bands at wavenumber of 1590 cm•1 (C=C) of alkene groups. The 1 H NMR spectra of all chalcone compounds showed a doublet proton signals with J = 12-15 Hz which interpreted as trans-alkene signal. Moreover, in the synthesis of compound 3, 7-methoxyflavanone, cis-3-(4-methoxy-phenyl)-1-phenyl-2-propenon, and 3- hydroxy-3-(4-methoxy-phenyl)-1-phenylpropanone were also obtained as side products.