SINTESIS 3-BENZIL-2-BUTIL-3-HIDROKSIISOINDOLIN-1-ON MELALUI REAKSI TERINDUKSI CAHAYA

NABILA AZZAHRA, Dr. M. Idham Darussalam Mardjan, S.Si., M.Sc.;Dr. Tri Joko Raharjo, M.Si.

2018 | Skripsi | S1 KIMIA

Sintesis 3-benzil-2-butil-3-hidroksiisoindolin-1-on melalui reaksi terinduksi cahaya telah dilakukan. Penelitian ini bertujuan untuk mempelajari pengaruh perlakuan terhadap sintesis 3-benzilidenftalida dan melakukan optimasi sintesis 3-benzil-2-butil-3-hidroksiisoindolin-1-on dengan memvariasikan jenis pelarut, jumlah amina dan perlakuan sintesis. Penelitian ini diawali dengan sintesis 3-benzilidenftalida dari asam 2-iodobenzoat dan fenil asetilena melalui reaksi Sonogashira katalis CuI dan garam NaHCO3 selama 24 jam. Reaksi dilakukan dengan tiga variasi perlakuan yaitu pemanasan pada 50 oC, kondisi gelap pada temperatur ruang dan radiasi sinar LED biru pada temperatur ruang. Produk 3-benzilidenftalida direaksikan dengan butil amina melalui reaksi adisi nukleofilik untuk mensintesis 3-benzil-2-butil-3-hidroksiisoindolin-1-on. Reaksi adisi nukleofilik dioptimasi dengan memvariasikan pelarut (DMSO dan iso-propanol), jumlah amina (1,3; 2; 3 ekuivalen), dan perlakuan (pemanasan 50 oC, gelap, radiasi LED biru). Produk dimurnikan dengan kromatografi kolom lalu dilakukan elusidasi struktur dengan spektrometer FTIR, GC-MS, 1H-NMR dan 13C-NMR. Hasil penelitian menunjukkan bahwa perlakuan radiasi LED biru paling optimum untuk sintesis 3-benzilidenftalida dengan hasil sintesis sebesar 64%. Sedangkan, kondisi optimum sintesis 3-hidroksiisoindolin-1-on diperoleh dengan menggunakan iso-propanol sebagai pelarut, 2 ekuivalen amina dan radiasi LED biru sebagai perlakuan sintesis. Dengan melakukan reaksi pada kondisi optimum, produk 3-benzil-2-butil-3-hidroksiisoindolin-1-on diperoleh dengan hasil sebesar 71% sebagai padatan kuning dengan titik leleh 134-136 oC.

Synthesis of 3-benzyl-2-butyl-3-hydroxyisoindolin-1-one via Photo-induced-Reaction has been conducted. The objectives of this research were to determine the optimum synthetic treatment of 3-benzylidenephthalide and to optimize the reaction conditions to synthesize 3-hydroxyisoindolin-1-one derivative including type of solvent, amount of amine and treatments. This research was initiated by synthesizing 3-benzylidenephthalide from 2-iodobenzoic acid and phenylacetylene via Sonogashira coupling reaction using CuI as catalyst and NaHCO3 as base for 24 hours. The reaction was performed using three different treatments, including heating at 50 �, dark condition and blue LED light radiation at room temperature. Preparation of 3-benzyl-2-butyl-3-hydroxyisoindol-1-one via nucleophilic addition between 3-benzylidenephthalide and butylamine. Nucleophilic addition reaction was optimized using various of solvents (DMSO and iso-propanol), amount of amine (1,3; 2; 3 equivalent) and treatments (heating at 50 �, dark condition and blue LED light radiation at room temperature). The products were finally purified using column chromatography, then elucidated using spectrometer FTIR, GC-MS, 1H-NMR and 13C-NMR. The results showed that blue LED light radiation was the optimum treatment to synthesize 3-benzylidenephthalide with the yield of 64%. In addition, the optimum conditions to generate 3-hydroxyisoindolin-1-on were obtained using iso-propanol as solvent, 2 equivalent of amine and blue LED light radiation as synthesis treatment. By performing the reaction under the optimum conditions, 3-benzyl-2-butyl-3-hydroxyisoindol-1-one was afforded as yellow solid with the melting point of 134-136 oC in yield of 71%.

Kata Kunci : 3-benzilidenftalida, 3-hidroksiisoindolin-1-on, adisi nukleofilik, reaksi Sonogashira, reaksi terinduksi cahaya.