Sintesis (Z)-3-Benzilidenisoindolinon Melalui Reaksi One-Pot

Dewi Anatasya Hapsari, Dr. M. Idham Darussalam Mardjan, M.Sc. ; Prof. Dr.rer.nat. Harno Dwi Pranowo, M.Si.

2019 | Skripsi | S1 KIMIA

Telah dipelajari sintesis (Z)-3-benzilidenisoindolinon berbahan dasar amonium asetat melalui reaksi one-pot. Tujuan dari penelitian ini untuk melakukan sintesis 3-benzilidenftalida melalui reaksi kopling Sonogashira dan mensintesis (Z)-3-benzilidenisoindolinon melalui reaksi dua tahap dan reaksi one-pot yang terdiri dari reaksi adisi nukleofilik dan Beta-eliminasi. Penelitian ini dilakukan dengan mensintesis 3-benzilidenftalida dari asam 2-iodobenzoat, fenilasetilena, terkatalis CuI pada temperatur ruang selama 24 jam. Selanjutnya, sintesis (Z)-3-benzilidenisoindolinon dilakukan melalui reaksi dua tahap dan reaksi one-pot. Sintesis (Z)-3-benzilidenisoindolinon melalui reaksi dua tahap dilakukan dengan mereaksikan 3-benzilidenftalida dan amonium asetat melalui reaksi adisi nukleofilik menghasilkan 3-benzil-3-hidroksiisoindolinon. Selanjutnya, 3-benzil-3-hidroksiisoindolinon direaksikan dengan HCl 6M melalui reaksi Beta-eliminasi menghasilkan (Z)-3-benzilidenisoindolinon. Sedangkan, sintesis (Z)-3-benzilidenisoindolinon melalui reaksi one-pot dilakukan dengan menggabungkan reaksi adisi nukleofilik dan Beta-eliminasi dilakukan dalam satu wadah. Produk hasil dikarakterisasi dengan titik lebur, spektrometer 1H-NMR, 13C-NMR, dan FTIR. Hasil penelitian menunjukkan bahwa 3-benzilidenftalida berhasil disintesis melalui reaksi kopling Sonogashira dengan persen hasil sebesar 64%. Sintesis (Z)-3-benzilidenisoindolinon melalui reaksi dua tahap berhasil disintesis dengan persen hasil reaksi adisi eliminasi dan Beta-eliminasi masing masing sebesar 70% dan 77%, sehingga persen hasil total dari reaksi dua tahap yaitu 54%. Produk (Z)-3-benzilidenisoindolinon berhasil disintesis melalui reaksi one-pot dan diperoleh persen hasil sebesar 73%. Dengan membandingkan persen hasil reaksi dua tahap dan reaksi one-pot didapatkan bahwa sintesis (Z)-3-benzilidenisoindolinon melalui reaksi one-pot lebih baik. Reaksi one-pot terbukti efektif, efisien, dan menerapkan prinsip green chemistry.

Synthesis of (Z)-3-benzylidenisoindolinone from ammonium acetate via one-pot reaction has been studied. The objectives of this research were to synthesize 3-benzylidenphtalide via Sonogashira coupling and to synthesize (Z)-3-benzylidenisoindolinone through two-step of reaction and one-pot reaction comprising nucleophilic addition and Beta-elimination reactions. This research was initially conducted by synthesizing 3-benzylidenphtalide from 2-iodobenzoic acid, phenylacetylene, in the present CuI catalyzed at room temperature for 24 h. Synthesis (Z)-3-benzylidenisoindolinone was conducted by two methods. Synthesis of (Z)-3-benzylidenisoindolinone through a two-stage reaction was carried out by reacting 3-benzylidenftalide and ammonium acetate through nucleophilic addition reactions to produce 3-benzyl-3-hydroxyisoindolinone. Next, Beta-elimination reaction was performed by heating 3-benzyl-3-hydroxyisoindolinone with HCl 6M to give (Z)-3-benzylidenisoindolinone. In one-pot reaction, the nucleophilic addition and Beta-elimination reactions were performed in one-pot fashion. The products ware characterized by melting point analysis, 1H-NMR, 13C-NMR, and FTIR spectrometers. The results showed that 3-benzilidenphtalide was synthesized via the Sonogashira coupling reaction in 64% yield. Synthesis of 3-benzylidenisoindolinone via two-step reaction was conducted with the yield of the nucleophilic addition and Beta-elimination reactions were of 70% and 77%, respectively. The total yield of (Z)-3-benzylidenisoindolinone synthesis through two-step reaction was 54% yield. The (Z)-3-benzylidenisoindolinone was obtained through a one-pot reaction in 73% yield. By comparing the yield of the two-step reaction and the one-pot reaction, the latter gave desired product in higher yield. One-pot reaction is proven to be effective, efficient, and apply the principles of green chemistry.

Kata Kunci : Kata kunci : turunan isoindolinon, one-pot, kopling Sonogashira, adisi nukleofilik, dan beta-eliminasi.