SINTESIS 2'-METOKS1 FLAVON O-HIDROKSI ASETOFENON DENGAN METIL SALISILAT (SYNTHESIS OF 2=METHOXY FLAVONE FROM 0-HYDROX ACETOPHENONE WITH METHYL SALICYLATE)
| Main Author: | Perpustakaan UGM, i-lib |
|---|---|
| Format: | Article NonPeerReviewed |
| Terbitan: |
[Yogyakarta] : Universitas Gadjah Mada
, 2001
|
| Subjects: | |
| Online Access: |
https://repository.ugm.ac.id/24737/ http://i-lib.ugm.ac.id/jurnal/download.php?dataId=7715 |
Daftar Isi:
- ABSTRACT The synthesis of flavone from o-hydroxy acetophenone with methyl salicylate has been conducted. The reaction sequence consisted of 3 stages i.e. : (1) methylation of methyl salicylate, (2) crossed Claisen condensation between o-hydroxy acetophenone with o-methoxy methyl benzoate to yield a diketone compound, and (3) reaction of the diketone with glacial acetic acid in the presence of concentrated sulfuric acid. Methylation of methyl salicylate was carried out using dimethyl sulfate (DMS) in the presence of sodium methoxide in methanol at 100C for 45 minutes. o-Methoxy methyl benzoate having 100 % purity was obtained in 77.12 % yield. Crossed Claisen condensation between o-hydroxy acetophenone with o-methoxy methyl benzoate was performed in some mol ratios of the reactants using sodium methoxide as the base at160°C for 30 minutes. The result of the experiment indicated that 1 : 6 mol ratio of o-hydroxy acetophenone with o-methoxy methyl benzoate was the best mol ratio which gave the diketone compound having purity of 86.52 % in 92.23 % yield. The diketone compound was then reacted with glacial acetic acid catalyzed by concentrated sulfuric acid at 1180C for 2.5 hours. 2' -Methoxy flavone which was 90.49 % purity was obtained in 55.61 % yield. The purity of the product was analysed using GC, whereas the structure was proven by means of IR, 1H NMR and GC-MS spectrophotometers. Key Words : methyl salicylate, o-Hidroxy acetophenone, diketone, flavon