SYNTHESIS OF 4-ALLYL-2-METHOXY-6-AMINOPHENOL FROM NATURAL EUGENOL

I Made Sudarma (Laboratory of Chemistry, Faculty of Mathematics and Natural Sciences, Mataram University Jl. Majapahit 62 Mataram 83125)
Maria Ulfa (Laboratory of Chemistry, Faculty of Mathematics and Natural Sciences, Mataram University Jl. Majapahit 62 Mataram 83125)
Sarkono Sarkono (Laboratory of Chemistry, Faculty of Mathematics and Natural Sciences, Mataram University Jl. Majapahit 62 Mataram 83125)

Indonesian Journal of Chemistry
Vol 9, No 1 (2009)

The aim of this preliminary research was to synthesize derivatives of eugenol such as 4-allyl-2-methoxy-6-nitrophenol (2) and 4-allyl-2-methoxy-6-aminophenol (3). The result could be used as a reference on the transformation of eugenol to its derivatives. Theoriticaly nitration of eugenol (1) by nitric acid could produced 4-allyl-2-methoxy-6-nitrophenol (2) and followed by reduction could achieved 4-allyl-2-mehtoxy-6-aminophenol (3). The formation of this product was analyzed by analytical thin layer chromatography (TLC) and GC-MS. These analysis showed the formation of product (2) and (3) were visible. TLC showed product (1) less polar than eugenol and gave orange colour, and supported by GC-MS which showed molecular ion at m/z 209 due to the presence of -NO2 by replacing one H at 6 position of eugenol. Product (3) was afforded by reduction of (2) with Sn/HCl and tlc analysis showed compound (3) more polar than eugenol (1) and (2) and supported by GC-MS which showed molecular ion at m/z 179 due to the presence of -NH2.