SINTESIS SENYAWA TABIR SURYA TURUNAN KALIKS[4]RESORSINARENA BENZOFENON DARI VANILIN SYNTHESIS OF SUNSCREEN COMPOUND OF CALIX[4]RESORCINARENE BENZOPHENONE DERIVATIVES FROM VANILLIN

Timur Setyawan, Jumina

2013 | Disertasi | PROGRAM STUDI S2 ILMU KIMIA

Synthesis of benzoyl C-3,4-dimethoxyphenylcalix[4]resorcinarene from vanillin has been carried out in five reaction steps. The structure elucidation of the products was performed by FTIR, 1H-NMR and GC-MS spectrometers. Then, the sun protection factor (SPF) of the final products was determined using UV-Vis spectrophotometer. The first step reaction was methylation of vanillin with dimethyl sulfate under basic condition by refluxing the mixture for 2h to give 3,4-dimethoxybenzaldehyde in 89% yield. The second step was reaction between 3,4-dimethoxybenzaldehyde and resorcinol in the presence of HCl catalyst in ethanol solvent at 78 oC for 24h to give C-3,4,-dimethoxyphenylcalix[4]resorcinarene in 98% yield. The third was acidcatalyzed- esterification of C-3,4-dimethoxyphenylcalix[4]resorcinarene with acetic anhidride to produce C-3,4-dimethoxyphenylcalix[4]resorcinarene octaacetate in 80% yield. The fourth step was benzoylation Friedel-Crafts of previous products with benzoyl chloride to afford benzoyl C-3,4-dimethoxyphenylcalix[4]resorcinil octaacetate in 73% yield. The fifth was hydrolysis the product of benzoylation with sodium hydroxide to produce benzoyl C-3,4-dimethoxyphenylcalix[4]resorcinarene in 97% yield. Characterization of benzoyl C-3,4-dimethoxyphenylcalix[4]resorcinarene using UV-Vis spectrophotometer showed that it has a maximum wavelength at 288 nm, indicating that it can be used as sunscreen compound UV-C and near UV-B. The SPF value of the synthesized calix[4]resorcinarene at the concentration of 2 ?g/mL

Kata Kunci : Vanilin; Sunscreen; Benzofenon, Kaliks[4]resorsinarena