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j. Cosmet. Sci., 50, 91-98 (March/April 1999) Synthesis of new fragrances from 2-methylfuran. Part I JANUSZ NOWICKI and J(SZEF G6RA, Institute of Heavy Organic Synthesis, "Blachownia," Energetyk6w 9, 47-225 Kqdzierzyn-Kogle, Poland, and Institute of General Food Chemistry, Technical University of L6dz, Stefanowskiego 4/10, 90-924 oeddz, Poland. Synopsis The synthesis of new 2-methylfuran derivatives are described. Odor and physicochemical characteristics of all new compounds are also presented. INTRODUCTION 2-Methylfuran 1 is one of the furan intermediates manufactured on a large scale. It is the main byproduct in the process of hydrogenation of furfuryl aidehyde to furfuryl alcohol. Being low-priced and readily available in the market worldwide, 2-methylfu- ran is an attractive intermediate in light organic synthesis. A very interesting trend is the application of 2-methylfuran to the synthesis of fra- grances. There are several reports on this subject. 2-Methylfuran is known to readily undergo on electrophilic type of condensation. Condensation with acetaldehyde in cer- tain weight ratios leads to the formation of 1,1-(5-methylfurfuryl)-ethane 2 (Figure 1), which has a citrus-flower fragrance (1). 271 U + + CH3CHO • Figure 1. In the Friedel-Crafts reaction with acid anhydrides, acylfuranes 3 are obtained (Figure 2): i R3 O O••2 3 1 O R• Figure 2. 91