Please use this identifier to cite or link to this item:
http://repository.ipb.ac.id/handle/123456789/114676
Title: | Transformasi Eugenol Menjadi Ester Koniferil Melalui Rangkaian Reaksi Proteksi-Brominasi-Esterifikasi |
Other Titles: | Transformation of Eugenol to Coniferyl Esters Through a Series of Protection-Bromination-Esterification Reactions |
Authors: | Arifin, Budi Sugita, Purwantiningsih Syahbani, Shifa Nur |
Issue Date: | 2022 |
Publisher: | IPB University |
Abstract: | Eugenol (4-alil-2-metoksifenol) adalah komponen utama minyak atsiri
cengkih. Transformasi eugenol menjadi ester koniferil dimungkinkan karena
keduanya memiliki kerangka fenilpropanoid yang sama. Penelitian ini melaporkan
transformasi 3 langkah eugenol menjadi ester koniferil. Pertama, eugenol diasetilasi
dan dibenzoilasi dengan menggunakan anhidrida asetat dan benzoil klorida serta
basa dengan rendemen berturut-turut 92% dan 97% dari eugenol. Kedua, reaksi
eugenil asetat dan eugenil benzoat dengan bromin dalam kloroform mengubah
rantai samping alil menjadi gugus 2,3-dibromopropil. Produk dibromida asetat dan
benzoat didapatkan dengan rendemen masing-masing 93% dan 90%. Ketiga, reaksi
esterifikasi juga berhasil dilakukan pada kedua dibromida, dengan pendekatan
melalui dehidrobrominasi dan substitusi nukleofilik dengan asam. Rendemen ester
dari eugenil asetat adalah 56% dan 39%. Kedua ester koniferil dari eugenil benzoat
diperoleh dengan rendemen 43% dan 49%. Ketiga reaksi dengan pemurnian tunggal
juga telah dirangkai untuk ester asetat dari eugenil asetat, dengan rendemen 45%.
Semua produk sintetik telah dikonfirmasi strukturnya secara spektroskopi. Eugenol (4-allyl-2-methoxyphenol) is the main component of clove essential oil. The transformation of eugenol to coniferyl esters is possible because both have the same phenylpropanoid framework. This study reports a 3-step transformation of eugenol to coniferyl esters. First, eugenol was acetylated and benzoylated successfully using acetic anhydride and benzoyl chloride, respectively, giving 92% and 97%. Secondly, the reaction of eugenyl acetate and eugenyl benzoate with bromine in the chloroform converts the allyl side chain to a 2,3-dibromopropyl group. Dibromide acetate and benzoate products yielded 93% and 90%, respectively. Thirdly, esterification reactions were also successfully carried out in both dibromides through dehydrobromination and nucleophilic substitution with acid. The two coniferyl esters of eugenyl acetate led to 56% and 39% yield. The two coniferyl esters of eugenyl benzoate were 43% and 49% yield. The three reaction series with single purification have also been assembled for the acetate ester of eugenyl acetate, and the yield was 45%. The structures of all the synthetic products have been confirmed spectroscopically. |
URI: | http://repository.ipb.ac.id/handle/123456789/114676 |
Appears in Collections: | UT - Chemistry |
Files in This Item:
File | Description | Size | Format | |
---|---|---|---|---|
Cover, Lembar Pernyataan, Abstrak, Lembar Pengesahan, Prakata dan Daftar Isi.pdf Restricted Access | Cover | 410.74 kB | Adobe PDF | View/Open |
G44180105_Shifa Nur Syahbani.pdf Restricted Access | Fullteks | 3.76 MB | Adobe PDF | View/Open |
Lampiran.pdf Restricted Access | Lampiran | 2.6 MB | Adobe PDF | View/Open |
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.