Sintesis C-Metil-4,10,16,22-Tetrametoksi Kaliks[4]arena dari Fenol Menggunakan BF3-Metanol Sebagai Katalis
ABSTRACT: C-Methyl
4,10,16,22-tetramethoxycalix[4]arene has been synthesized from phenol. The
reaction performed consisted of methylation of phenol, acetylation of methyl
phenyl ether, reduction of p-methoxyacetophenone, and cyclization of
p-methoxy-(1-hydroxyethyl)benzene to form
C-methyl-4,10,16,22-tetramethoxycalix[4]-arene using BF3-methanol as the acid
catalyst. Methylation of phenol was done
by reacting phenol with solution of NaOH to generate sodium phenoxide salt.
This mixture was strirred at reflux for
0.5 hours. Dimethyl sulphate was added and the reflux was continued for 2,5
hours. The product obtained was methyl phenyl ether, which was found as a colorless liquid in 99.0% yield.
Acetylation of methyl phenyl ether was carried out in chloroform using acetic
anhydride as the acetylating agent and anhydrous aluminium chloride as the
catalyst. The addition of acetic anhydride and anhydrous aluminium chloride was
done in two portions. The first portion was 0.967 g of acetic anhydride and 1.4
g of anhydrous aluminium chloride. The second portion was 0.54 g of acetic
anhydride and 0.6 g of anhydrous aluminium chloride. The product obtained was
found as a reddish yellow liquid in 69.6% yield. Reduction of
p-methoxyacetophenone as the acetylation product was
done using NaBH4 in ethanol at reflux for 2.5 hours. From this reaction,
p-methoxy-(1-hydroxyethyl)benzene was obtained as a brown viscous liquid in
44.9% yield. Cyclization of p-methoxy(1-hydroxyethyl)benzene was done using
BF3-methanol as the acid catalyst for two days at room temperature. The product
obtained from this cyclization was found as a brown very viscous liquid in
87.3% yield. Identification of reaction products were carried out using Infra
Red (IR) Spectrophotometer, Proton Nuclear Magnetic Resonance (1H NMR)
spectrometer and Gas Chromatography-Mass spectroscopy (GC-MS).
Penulis: Jumina, Evi
Triwulandari, Chairil Anwar
Kode Jurnal: jpkimiadd050023
