THE STUDY OF (E)-2-((P-TOLYLIMINO)METHYL)PHENOL SYNTHESIS AND ITS REDUCTION TO 2-((P TOLYLAMINO)METHYL)PHENOL USING MICROWAVE ASSISTED ORGANIC SYNTHESIS (MAOS) METHOD

• Main Author: MAHARDIKA (NIM : 10508004); Pembimbing : Dr. Deana Wahyuningrum, MICHA
• Format: Final Project
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/16444
• Institution: Institut Teknologi Bandung

Nowadays, organic synthesis using microwave has been developed. This method begins to replace conventional method due to the belief that it can produce more yields, less amount of solvent and faster reaction time. In this study, there are two compounds that have been successfully synthesized: (E)-2-((p-tolylimino)methyl)phenol (compound 1) and 2-((ptolylamino) methyl)phenol (compound 2) with two methods: conventional and MAOS (Microwave Assisted Organic Synthesis) methods. Synthesis of compound 1 utilizing <br /> <br /> <br /> <br /> <br /> conventional method was carried out for 15 minutes while the MAOS method was only 5 seconds, with the yields and melting points of product for each method are 93.39% (m.p. 94-96 oC) and 97.17% (m.p. 93-95 oC), respectively. The compound 1 is then reduced with NaBH4 to produce 2-((p-tolylamino)methyl)phenol using 2 methods. By using the <br /> <br /> <br /> <br /> <br /> conventional method, it took 45 minutes to produce compound 2, while the MAOS method only took 25 seconds, with the yields and melting points for each method are 74.04% (m.p. <br /> <br /> <br /> <br /> <br /> 118-120 oC) and 75% (m.p. 120-122 oC), respectively. Those two compounds were analyzed by TLC using n-hexane:ethyl-acetate 1:1 as eluents and characterized by FTIR, UV-Vis, NMR and MS. Compound 1 and 2 have Rf values of 0.9 and 0.8, respectively. Compound 1 has a typical peak of IR vibration of C=N at 1718.75 cm-1 and C-N at 1218.75 cm-1, and UV absorption at 340 nm. The spectrum 1H-NMR and 13C-NMR of compound 1 has a typical chemical shifts of imine groups at 8.63 ppm and 161.88 ppm, respectively. Compound 1 has m/z 212.19 (ESI+) with molecular formula of C14H13NO. Compound 2 has a typical peak of IR vibration of N-H at 3265 cm-1 and C-N at 1220.25 cm-1, and UV absorption at 280 nm. The spectrum 1H-NMR and 13C-NMR of compound 2 has a typical <br /> <br /> <br /> <br /> <br /> amine chemical shifts at 4.40 ppm and 49.53 ppm. Compound 2 has m/z 214.23 (ESI+) with molecular formula of C14H15NO. Regarding to the results of this study, MAOS method <br /> <br /> <br /> <br /> <br /> produces the product of compound 1 and 2 with higher yields in a shorter reaction time compared to conventional method which fulfill most of the criterions of green chemistry.