Synthesis of 5-Hydroxy-4-methoxy-α-methyl-(1,2-benzobutane sultone) from Eugenol and Eugenil Acetate

I.M. Sudarma*, L. Supiani, A. Syafitri, W.K. Hidayati, H. Oltantia and M.G. Darmayanti

Department of Chemistry, Faculty of Mathematic and Natural Sciences, University of Mataram, Kota Mataram 83115, Indonesia

*Corresponding author: Fax: +62 370 648508; Tel: +62 370 646506; E-mail: sud_arma@yahoo.co.id

Abstract

The purpose of this study was to develop an efficient synthesis route to pharmacologically interesting sultone derivatives from readily accessed natural products. Synthetic approach of 5-hydroxy-4-methoxy-α-methyl-(1,2-benzobutane sultone) via eugenol (1) produced only in moderate yield (64 %). On the other hand synthetic approach via eugenil acetate (2) gave 5-hydroxy-4-methoxy-α-methyl-(1,2-benzobutane sultone) in high yield (96 %). Eugenol approach involved only one step reaction due to direct reaction of eugenol with chlorosulfonic acid but in eugenil acetate approach involved two-step reactions due to its preparation of eugenol before reaction with chlorosulfonic acid. Eugenil acetate was prepared smoothly in good yield by esterification of phenolic group of eugenol with acetic anhydride in the presence of sodium bicarbonate. A variety of bicarbonate catalysts such as NaHCO3, Na2CO3 and K2CO3 were investigated in O-acetylation of eugenol to afford eugenil acetate (84 %), (72 %) and (88 %), respectively. Structures of all the products have been established by spectral and GC-MS analysis data.

Keywords

Comparison reaction, Eugenol, Eugenil acetate, Cyclic sulfonic ester, Sultone, Markovnikov.

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