SYNTHESISOF FLAVANONE-6-CARBOXYLICACID DERIVATIVES FROMSALICYLIC ACID DERIVATIVE
| Main Author: | Perpustakaan UGM, i-lib |
|---|---|
| Format: | Article NonPeerReviewed |
| Terbitan: |
[Yogyakarta] : Universitas Gadjah Mada
, 2011
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| Subjects: | |
| Online Access: |
https://repository.ugm.ac.id/28547/ http://i-lib.ugm.ac.id/jurnal/download.php?dataId=11610 |
Daftar Isi:
- Synthesis of fIavanone-6-carboxylic acid derivatives had been conducted via the route of chalcone. The synthesis was carried out from salicylic acid derivative, i.e. 4-hydroxybenzoic acid, via esterification, Fries rearrangement, Claisen-Schmidt condensation and 1,4-nucleophilic addition reactions. Structure elucidation of products was performed using FT-IR, 1H-NMR, GC-MS and UV-Vis spectrometers. Reaction of 4-hydroxybenzoic acid with methanol catalyzed with sulfuric acid produced methyl 4-hydroxybenzoate in 87% yield. The acidcatalyzed- acetylation of the product using acetic anhydride gave methyl 4-acetoxybenzoate in 75% yield. Furthermore, solvent-free Fries rearrangement of methyl 4-acetoxybenzoate in the presence of AIC/3produced 3- acetyl-4-hydroxybenzoicacid as the acetophenonederivatives in 67%yield. Then, Claisen-Schmidtcondensation of the acetophenone and benzaldehyde derivatives of p-anisaldehyde and veratraldehydein basic condition gave 2'- hydroxychalcone- 5'-carboxylicacid derivatives in 81 and 71 %yield, respectively. Finally, the ring closure reaction of the chalconeyielded the co"esponding fIavanone-6-carboxylicacids in 67 and 59%yield, respectively.