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Hendra Wijaya
Center for agro-based Industry
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Journal : Makara Journal of Science

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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 Aliya Nur Hasanah Amir Amir Anabella, Christella Norica Andina, Ni Kadek Devi Pradnya Angelina, Ariyanthini Elisabeth Anggreini, Dwi Desi April Gunawan Malau Ardhani Dwi Lestari, Maria Lucia Arista Candra Irawati Bambang Widjaja Bella, Yova Berliani, Annisa Butar-Butar, Mangasi Calvin Calvin Choirunisa, Syifa Dandy Pramana Hostiadi Darmawan, Fiki Dwi Dewi Isadiartuti Dewi, Ni Putu Intan Satya Dwi Budi Santoso Eka Indra Setyawan ernikawati, ernikawati Evi Triandini Felix Pasila Feriwanti, Dwi Fitri Hasanah Gesti Memarista Gunawan, Erick Teofilus Haidir, Hala Handry Khoswanto Hutagaol, Jarunjung Intan Permatasari Jus'at, Idrus Katili, Yusril Kiwo, Diminus Lazuarni, Shafiera Lestari, Fitriana Dwi Lucy Simorangkir Lukman Hakim M Yusuf Marjono, Cornelia Clarissa Mastar Asran Miradz, Arik Moito, Febrianti Moonti, Roy Marthen Motik, Chandra Muhamad Azhar, Muhamad MUNAJIR, ACHMAD Naripradnya, Putu Saradevi Ngabito, Meriyanti Nurkholis, Kgs. M . Oktiani, Lita Aryati Panigoro, Nurmaya Parta, I Putu Rizki Karisma Pranata, Andri Pratama, Wahyu Riski Putri, Anastasia Aurelia Rahayu, Leni Ramadhan, Moh. Fauzan Rini Setiawati Rizky Nugroho Adji Rosiana, Febe Rudiyanto Rudiyanto, Rudiyanto S. Patricia Febrina Dwijayanti Samvara, Made Adhiguna Santoso Ratu, Dennis Setiasih Setiasih, Setiasih Sienny Thio Siregar, Julinda Sofian, Sofian Sukmawati . Sukri, Tony Surjaatmaja, Lukas Susanti, Aprillia Nanda Susanto, Hendro Sutri, Wiratama Kadek Thaib, Abdul Shamad Vamiati, Sri Virginia, Maria Vivi Bachtiar Wahyuning Astuti, Reny Winisudo, Christian Kevin Wira Udytama, I Wayan Wahyu Yanti, Rina Dwi Yogi Yasa Wedha Yoraeni, Ani