The Synthesis of 3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one and The Study of Its Transformation Using H202 in Ionic Liquid 1-0ctyl-3- Methylimidazolium Bromide ([OMim]Br) as Medium Utilizing Microwave Assisted Organic Synthesis (MAOS) Method

• Main Author: Liyanto, Henry
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/42016
• Institution: Institut Teknologi Bandung

Th e a, -un saturated carbon y l compounds or commonl y known as chalcone compounds are a subgroup of flavonoid compounds that have potent bioactivities. Several bioactivities of chalcone are anticancer, antibacterial, anti-inflammatory, anti-hyperglycemic, antiviral, and antimalarial agent. The market of flavonoid compounds is predicted to be increased until 2025, which causes flavonoid compounds to be in high demand and is needed by the market so that the way of production will continue to be developed. Chalcone derivative compounds synthesized in this study is 3- (2-hydroxyphenyl) -1-phenylprop-2-en-1-one, hereinafter referred to as compound L which is the result of the reaction between salicylaldehyde and acetophenone in the ionic liquid medium utilizing Microwave Assisted Organic Synthesis (MAOS) method. The ionic liquid used as a medium in this reaction is the imidazole derivative ionic liquid , which is 1-octyl-3-methylimidazolium bromide ([OMim]Br). The ionic liquid was synthesized by reacting 1-methylimidazole with octylbromide using MAOS method at 50 °C and 300 W irradiation power for 60 minutes with chemical yields of 73.00%. Compound 1 was synthesized by reacting acetophenone and salicylaldehyde with a ratio of I: 1.05 mole in [OMim)Br ionic liquid: water= I :20 (w/v) as medium and in alkaline condition using MAOS method (P = 300W, T = 60 °C for I 0 minutes) to yields 65.09%. The melting point of compound 1 is 152-153 oc. The structure confirmation of compound 1 was determined by using IR spectroscopy (showed the presence of C=C vibration at 1597.21 cm- 1 ) and NMR spectroscopy corresponding to the structure of chalcone compound with trans coupling (J = 15.0 Hz). Compound 1 was further transformed using H 202 in alkaline condition using [OMim)Br ionic liquid : water = I :20 (w/v) as medium, which underwent Dakin oxidation, resulting in benzo ic acid -with a y ield of 63.64%. Confinnation of product structure was obtained by IR and NMR spectroscopy which corresponded to the structure of benzoic acid.