EFFECTS OF ETHYLENE GLYCOL AND KOH IN THE FORMATION OF 2-METHOXY-4-PROPYLPHENOL ON EUGENOL ISOMERIZATION REACTION

https://doi.org/10.22146/ijc.21841

Muchalal Muchalal(1*)

(1) Chemistry Department, Faculty of Mathematics and Natural Sciences Gadjah Mada University, Yogyakarta
(*) Corresponding Author

Abstract


Formation reaction mechanism of  2-methoxy-4-propylphenol on eugenol isomerization that involved protic hydrogen originated from ethylene glycol as a solvent has been done. To check this reaction mechanism, the effect of amounts of ethylene glycol as a solvent and KOH as a reagent on the quantity of 2-methoxy-4-propylphenol as a product has been carried out. The reaction product was analyzed by GC and GC-MS. Quantity of 2-methoxy-4-propylphenol as a product increased if ratio of quantity of ethylene glycol as solvent to quantity of KOH as reagent became larger. The result showed that formation process of 2-methoxy-4-propylphenol involved the protic hydrogen of solvent. The existence of cis-isoeugenol as an initiator compound in forming 2-methoxy-4-propylphenol indicated that the reaction mechanism followed the steps (1) cis-isoeugenolic ion gave Cb with negative charge at prophenyl group through resonance (2) a negative charge Cb then attacked a protic H atom in the solvent, and (3) hydride ion will attack Cb to form 2-methoxy-4-propylphenolic ion.


Keywords


2-methoxy-4-propylphenol; ethyleneglycol - KOH

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References

[1] Lampman, G.M., Andrews, J., Bratz, W., Hassen, O., Kelley, K., Perry, D., and Ridgeway, A., 1977, J. Chem. Educ, 54(12), 776 – 778

[2] Lampman, G.M. and Sharpe, S.D., 1983, J. Chem. Educ, 60(6), 503 - 504

[3] Sastrohamidjojo, H., 1981, A Study of Some Indonesian Essential Oils, Disertasi, FMIPA UGM, Yogyakarta

[4] Cerveny, L., Krejcikova, A., Marhoul, A., and Ruzicka, 1987, Catal. Let. 33(2), 471 – 476

[5] Peterson, T.H., Bryan, J.H., and Keevil, T.A., 1993, J. Chem. Educ, 70(4), A96 - A98

[6] Zucco, C., 1997, Syn. Communic. 27(24), 4335-43

[7] Muchalal, M. dan Respati Tri Swasono, 1999, Berkala Ilmiah MIPA, IX (1), 48 – 56

[8] Kadarohman, A., 2003, Isomerisasi, Hidrogenasi Eugenol, dan Sintesis Turunan Kariofilena, Disertasi, UGM, Yogyakarta.



DOI: https://doi.org/10.22146/ijc.21841

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Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

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