DERIVATISASI ANETOL HASIL ISOLASI MINYAK ADAS (Derivatization Of Anethole Isolated From Fennel Oil)

ABSTRACT The isolation and derivatization of anethole has been carried out. Anethole was obtained from fennel oil by fractional distillation at reduced pressure. The derivatization of anethole was conducted by oxidation with KMn04 at 40°C to give p-anisic acid (anethole:134n04 = 1:3 mole, for 2 hours) and p-anisaldehyde (anethole:KMnO4 = 1:2 mole, for 30 minutes). Furthermore, p-anisic acid was esterified and p-anisal¬dehyde was subjected to Canizzaro reaction, acetalization, and reduction. Derivatization of anethole was also carried out by alkilation of anethole with tert-butanol and A103. The esterification of p-anisic acid was carried out using methanol at 65°C for 4 hours to yield methyl p-anisate. The acetalization of p-anisal-dehyde was done using absolute ethanol and CaCl2 catalyst at 30°C, 50°C, and 75°C for 4 hours. The Canizzaro reaction of p-anisaldehyde was performed using KOH at 30°C for 2, 3, and 4 hours. The reduction of p-anisaldehyde was carried out using sodium and ethanol at 75°C for 5 hours to give p-anisyl alcohol. The alkilation of anethole with tert-butanol and AIC13 (anethole:tert-butanol: A1CI3 = 2:3:1 mole) was carried out at 35°C for 4 hours to give polyanethole. The GC-MS spectra showed that fennel oil contains limonene (2.35%), fenchon (32.09%), estragol (5.75%), p-anisaldehyde (12.24%), and anethole (40.33%). The yields of p-anisic acid and p-anisaldehyde obtained from the oxidation of anethole, as mentioned above, were 66.05% and 97.94%, respectively. The yields of methyl p-anisate, p-anisyl alcohol, and polyanethole were 62.77%, 81.09%, and 87.08%, respectively. p-Anisaldehyde was found stable toward Canizzaro reaction and acetalization. Key words : anethole, oxidation, esterification, reductio