Abstract—The main content of clove oil is eugenol, amounting to 80-90%. The aims this study to utilize eugenol from clove leave oil as raw material in the synthesis of 3,4-dimethoxybenzyl-2’,4’-dihydroxyphenyl ketone with 3,4-dimethoxybenzylcyanide as intermediate compound. Converting eugenol into 3, 4-dimethoxybenzyl cyanide via several stages of reactions. Methylation of eugenol using dimethylsulphate and NaOH as catalyst was produced methyleugenol as much as 89.78% with a purity of 93.6%. Isomerization of methyleugenol using alkaline potassium tertiary butoxide (t-BuOK) in the medium dimethyl sulfoxide (DMSO) was resulted in 87.24 % yield methylisoeugenol with a purity of 88.89%. Methylisoeugenol was oxydated using potassium dichromate (K2Cr2O7) in a phase transfer catalyst system (PTC) by Polysorbate 80 into a 3,4- dimethoxybenzaldehyde as much as 85.36 % with a purity 83.46 %. Reduction of 3.4-dimethoxybenzaldehyde using sodium borohidrat (NaBH4) was producted 3.4- dimethoxybenzylalcohol as much as 98 % with a purity 100 % level. The 3.4-dimethoxybenzylalcohol was halogenated using SOCl2 was producted 3.4-dimethoxybenzylchloride which reacted further with sodium cyanide to produce 3.4-dimethoxybenzylcyanide as much as 89.5 % with a purity 99.24%. The acylation reaction of acid 3,4-dimethoxyphenylacetic acid with resorcinol to 3,4-dimethoxybenzyl-2,4-dihydroxyphenyl ketone obtained is a white a solid product having a melting point of 171-172OC. Rendamen generated from this experiment by 76%.
Index Terms—Eugenol, 3.4–dimethoxybenzylcyanide, 3,4-dimethoxybenzyl-2’, 4’dihydroxyphenylketone.
Matsjeh S. and Anwar C. are with the Department of Chemistry, Faculty of Mathematics and Natural Sciences, Gadjah Mada University, Yogyakarta, Indonesia (e-mail : matsjeh@ugm.ac.id, irilwar@ugm.ac.id).
Sholikhah E. N. is with the Pharmacologi Department, Faculty of Medicine, Gadjah Mada University, Yogyakarta, Indonesia. Alimuddin A. A. is with the Department of Chemistry, Faculty of Mathematics and Natural Sciences, Tanjungpura University, Tanjungpura, Indonesia.
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Cite: Matsjeh S., Anwar C., Sholikhah E. N., and Alimuddin A. A., "Synthesis 3,4-Dimethoxybenzyl-2,4-Dihydroxyphenyl Ketone from Eugenol," International Journal of Chemical Engineering and Applications vol. 6, no. 1, pp. 61-65, 2015.
