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Journal : Makara Journal of Science

REAKSI PENATAAN ULANG SIGMATROPIK HIDROGEN [1,3] SECARA TERMAL DAN REAKSI PENATAAN ULANG PROTOTROPIK [1,3] YANG DIKATALISIS OLEH KATALIS TRANSFER FASE (PTC) , [18]-CROWN ETHER-6: SEMI-SINTESIS VANILI DARI EUGENOL* Suwarso, Wahyudi Priyono; Sukri, Tony; Wijaya, Hendra
Makara Journal of Science Vol. 6, No. 1
Publisher : UI Scholars Hub

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Abstract

Semi-synthesis of vanillin from eugenol can be divided into two step reactions namely, isomerization of eugenol into isoeugenol, and cleavage oxidation of isomerization product into expected reaction product (vanillin). In this work isomerization of eugenol or eugenyl acetate into isoeugenol or isoeugenyl acetate has been done via the following reactions: (1) Sigmatropic hydrogen (1,3) thermalic rearrangement reaction: direct heating of eugenol or eugenyl acetate at 220o C for 8 hours can produce 52.2% of isoeugenol or 65.7% of isoeugenyl acetate (both chemical yields are measured by means nmr-spectrometer), where products are viscose yellow-brownish liquid as mixture of unseparated starting material and isomerization product. (2) Prototropic (1,3) rearrangement catalyzed by phase transfer catalyst (PTC): (18)-crown ether-6 at room temperature can be afforded 71.4% of isoeugenol as light yellow liquid (mixture of unseparated starting material and isomerization product). Without any separation of mixture between isomerization product and starting material followed by subsequent cleavage oxidation using KMnO4 as oxidator in neutral condition catalyzed by phase transfer catalyst: (18)- crown ether-6 at room temperature for 3 hours can be yielded 16.5-22.9% of vanillin (from the starting material; eugenol or eugenyl acetate). The spectroscopical data of synthetical vanillin is not rather different with the spectroscopical data of authentical natural vanillin
Co-Authors Abdul Syukur Ade Pratama Ade Suherman Adityo Fajar Nugroho Adityo Fajar Nugroho Adityo Fajar Nugroho Akemi Ito Aliya Nur Hasanah Amir Amir Anabella, Christella Norica Andina, Ni Kadek Devi Pradnya Angelina, Ariyanthini Elisabeth Anggreini, Dwi Desi Angraini, Novi Annisa Thaharah Anwar, Chaerul April Gunawan Malau Ardhani Dwi Lestari, Maria Lucia Arista Candra Irawati Bambang Widjaja Bella, Yova Berliani, Annisa Butar-Butar, Mangasi Calvin Calvin Candy Candy Choirunisa, Syifa Dandy Pramana Hostiadi Darmawan, Fiki Dwi Darwin Darwin Dewi Isadiartuti Dewi, Fitriya Nur Annisa Dewi, Ni Putu Intan Satya Dudung Angkasa Dwi Budi Santoso Eka Indra Setyawan Ela Turmala Sutrisno Endang Prangdimurti Erka Fitria ernikawati, ernikawati Evi Triandini Febriyanti, Erna Felix Pasila Feriwanti, Dwi Fitri Hasanah Fitri Hasanah Fitri Hasanah Fransiska Zakaria Rungkat Gesti Memarista Goto, Manami Gunawan, Erick Teofilus H.G Pohan Haidir, Hala Handry Khoswanto Haruka Miyakita Hidekazu Shigematsu Hutagaol, Jarunjung Ika Kurnia Siswawati Indra Neffi Ridwan Inggrid S. Surono Intan Permatasari Ir. Lukman Junaidi Ito, Akemi Johny Budiman Junaidi, Lukman Jus'at, Idrus Katili, Yusril Kiwo, Diminus Lazuarni, Shafiera Lestari, Fitriana Dwi Lucy Simorangkir Lukman Hakim Lukman Junaidi Lusiana Lusiana M Maman Rohaman M Yusuf Maeda, Takanori Malino, Ahmad Esa Galang Maman Rohaman, M Manami Goto Maria Novelina.S, Yus Marjono, Cornelia Clarissa Mastar Asran Miradz, Arik Miyakita, Haruka Moito, Febrianti Moonti, Roy Marthen Motik, Chandra Muhamad Azhar, Muhamad MUNAJIR, ACHMAD Nami Lestari Naripradnya, Putu Saradevi Neffi Ridwan, Indra Ngabito, Meriyanti Ning Ima Arie Wardayanie Ning Ima Arie Wardayanie Nishigaki, Toshiaki Nur Wulandari Nurkholis, Kgs. M . Oktiani, Lita Aryati Olivia, Novie Panigoro, Nurmaya Parta, I Putu Rizki Karisma Pohan, H.G Pranata, Andri Pratama, Wahyu Riski Purwiyatno Hariyadi Putri, Anastasia Aurelia Rahayu, Leni Rahmad Arif Raisa Shafira Jarief Ramadhan Ningrum Has, Dinia Ramadhan, Moh. Fauzan Reno Fitri Hasrini Rhoito Frista Silitonga, S.Si Rini Setiawati Rizki Maryam Astuti Rizky Nugroho Adji Rosiana, Febe Rudiyanto Rudiyanto, Rudiyanto S. Patricia Febrina Dwijayanti S. Surono, Inggrid Samvara, Made Adhiguna Santi Ariningsih Santi Ariningsih, M.Si Santoso Ratu, Dennis Setiasih Setiasih, Setiasih Shigematsu, Hidekazu Sienny Thio Siregar, Julinda Sofian, Sofian Sofian, Sofian Sri Yadial Chalid Sriyogasari, Titin Stewendy, Stewendy Suherman, Ade Sukmawati . Sukri, Tony Surjaatmaja, Lukas Susanti, Aprillia Nanda Susanto, Hendro Sutri, Wiratama Kadek Takanori Maeda Thaib, Abdul Shamad Titin Sriyogasari Toshiaki NISHIGAKI Toshiaki Nishigaki Toshiaki Nishigaki Turmala Sutrisno, Ela Vamiati, Sri Virginia, Maria Vivi Bachtiar Wahyuning Astuti, Reny Widyaningsih Widyaningsih Wijaya, Frendy Winisudo, Christian Kevin Wira Udytama, I Wayan Wahyu Yanti, Rina Dwi Yogi Yasa Wedha Yoraeni, Ani Yus Maria Novelina.S