NEW FRAGRANCES FROM 2-METHYLFURAN: I 93 •CH2OH R1 5 7a: R•, R2=H 7b ' R•=CH 3, R2=H 7c: R•=H, R2=C2H 5 ••R1R20Tø• 7 Figure 5. As another step in the Grignard reaction of aldehydes 4 with methylmagnesium iodide, alcohols 8, and their acetates 9 were obtained (Figure 6): O AcONa R1 4 8 9 8a, 9a: R•=CH 3, R•=H 8b, 9b ß R•-H, R•=C•H 5 EXPERIMENTAL Figure 6. Purity of the obtained new compounds reached 98% and their structures were confirmed by IR and •H-NMR spectra. IR spectra were obtained in a Perkin-Elmer spectrometer Model SP-1000: Gas chromatographic analyses were performed using a Perkin-Elmer chromatograph Model 900 (column 1.8 m, LAC 2R, 15% on chromosorb WAW 60/80 mesh, temperature 80-195øC, argon as a carrier gas). •H-NMR spectra were obtained in a Hitachi-Perkin-Elmer spectrometer R24A (80 MHz, CC14, TMS). The reactions were controlled by TLC developed with a 9:1 hexane-acetone mixture. Aldehydes 4a-c were prepared according to the procedure described in the literature (5), with a yield of 45-66%. GENERAL PROCEDURE FOR PREPARATION OF ALCOHOLS 5 The selected aldehyde 4 (0.47 mole) was dissolved in methanol (200 cm 3) with con- tinuous stirring, and a solution of NaBH 4 (4 g) in 10% NaOH (80 cm 3) was slowly added dropwise with cooling. The reaction medium was stirred for one hour at 40-50øC. After evaporation of the major part of the methanol, water (50 cm 3) was added followed by phase separation. The aqueous phase was extracted with toluene (2 x 50 cm3). The

Table I Odor Characteristic of New Furan Compounds Lp. Compound Odor characteristic •x-./'•CH20 H 2 •CH2OH 5b Intense and fresh, floral-fru 5a Intense and fresh, with a note of fresh yeast •H2OH 5c Intense, floral similar to the fragrance of Liliam candida 10 ••L'x..'"•CH2OAc /•'•CH2OAc •CH2OAc •L--..-"•CH2OPr •-•CH2OP r •CH2OPr 6a Intense, mushroom-floral with a note of yeast 6b 6c 6d 6e Intense, fresh, similar to the fragrance of lilac and tuberose Intense, fresh, fruity-floral, similar to the fragrance of dwarf Japanese quince Pleasant, fruity-floral with a note of wild strawberry Intense, fresh, fruity-floral with a mild note of rose 6f Pleasant, fresh, floral with a note of calamus and coumarine 7a Intense, pleasant, floral with a note of spice 11 12 13 14 o.T.o 7b Intense, pleasant, floral with a note of lupine 7c Very intense, not interesting 8b Intense, pleasant, floral with a note of rose 8c Pleasant, fresh, fioral-fruity with a note of rose