APPLICATION OF NICKEL CATALYZED C-C COUPLING REACTION FOR THE SYNTHESIS OF ORYCTES RHINOCEROS L. PHEROMONE COMPOUNDS ETHYL 4-METHYLOCTANOATE

• Main Author: Nur Khaeruni, Annisa
• Format: Theses
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/62819
• Institution: Institut Teknologi Bandung

Ethyl 4-methyloctanoate is a male pheromone of rhinoceros beetle insect (Oryctes rhinoceros). The rhinoceros beetle is a severe pest of coconut plants. This pest is able to reduce the productivity of coconut plants and in many cases can kill the plants. In this research, ethyl 4-methyloctanoate has been detected as product from two steps synthesis, namely the hydrobromination step of 1-hexene using HBr and the carbon-carbon coupling reaction step between ethyl acrylate and 2- bromohexene in presents of the catalyst (PPh3)2NiCl2. The hydrobromination reaction of 1-hexene took place at room temperature to produce 2-bromohexane as a mixture with 1-bromohexane with composition of 61:39. Furthermore, the key step of Ni-catalyzed C-C coupling reaction between 2-bromohexane and ethyl acrylate took place at a temperature of 65 ?C to furnish the target in a mixture of crude reaction. The ethyl 4-methyloctanoate have been identified by intensive analysis of spectroscopies data 1H-NMR, 13C-NMR, and GC-MS. Based on GC chromatogram analysis, it was shown that the ethyl 4-methyloctanoate have been successfully obtained through this strategy with a concentration of 14,28% in the reaction mixture.