Synthesis of Eugenoxy Acetic Acid from Eugenol Utilizing Microwave Assisted Organic Synthesis (MAOS) Method

• Main Author: Ayu Andhira, Bonita
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/32276
• Institution: Institut Teknologi Bandung

Eugenoxy acetic acid (IUPAC name: 2-methoxy-4-(2-propenyl)phenoxyacetic acid) is a compound of odorless, colorless and noncytotoxic. These compounds are known to have antiviral and antibacterial property, so it is used as an antioxidant preservative in the food industry. In this experiment, eugenoxy acetic acid is synthesized from eugenol derived from clove oil reacted with monochloroacetic acid using MAOS (Microwave Assisted Organic Synthesis) method. Eugenol was treated in alkaline conditions by adding NaOH and then put into the domestic microwave oven with irradiation power of 800 W for 10 seconds. The acetate environment was obtained from monochloroacetic acid which way reacted with sodium carbonate. The reaction mixture was reacted in MAS-II SINEO microwave oven reactor under irradiation power of 300 W at 70 °C for 1 minute to produce eugenoxy acetic acid with chemical yields 95.14% and having melting point of 78 oC.The product characterization was performed using infrared spectroscopy measurementto obtainC=O peak of –COOH at wavenumber of 1748 cm-1, cluster ring C=C of benzene peak at (1581, 1514, 1448) cm-1, and the peak of the eter group C-O-C at 1255 cm-1. The analysis of1H NMR (500 MHz, in CDCl3) spectra showed the presence of clusters benzene rings at the chemical shift of 6.82, 6.81, and 6.70 ppm, a singlet signal corresponds to methyl protons of methoxyl groupat 4.65 ppm, doublet signals in the alkene group protons at 5.08 ppm, and a singlet signal of -OH group at 5.06 ppm. The analysis of 13C NMR spectra (125 MHz, in CDCl3) indicatedthe presence of 12 carbon signals withchemical shifts that correspond to the functional groups within eugenoxy acetic acid structure. The mass spectroscopy measurement using Electronspray Ionization (ESI-MS, HRMS TOF MSES-) showed the presence of peak of [M-H+] 221.0813 that corresponds to the molecular formulae of C12H14O4, which is the molecular formula of eugenoxy acetic acid.