SYNTHESIS OF FRAGRANCES FROM 2-METHYLFURAN 495 /"•••CHO R• 2 Pd/C cyclohexene Figure 4 /••L•cH O R• 6a,b 6a:Rl=H 6b: Ri = CH3 /"•••'••CHO R• 6 NaBH4 NaOH/MeOH Figure 5 7a,b 7a: R1 = H 7b:R1 = CH3 /'•••CHO R1 CH3MgJ Figure 6 8a,b 8a:Rl=H 8b: Rl = CH3 EXPERIMENTAL The purity of the obtained new compounds reached 98% and their structures were confirmed by IR and Z H-NMR spectra. IR spectra were obtained with 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 chromo- sorb WAW 60/80 mesh, temperature 80ø-195øC, argon as carrier gas]. Z H-NMR spectra were obtained with a Hitachi-Perkin-Elmer spectrometer R24A (80 MHz, CC14, TMS). The reactions were controlled by TLC developed with a 9:1 hexane-acetone mixture. The physicochemical characteristics of the new compounds are collected in Table II. GENERAL PROCEDURE FOR PREPARATION OF ALDEHYDES 2 AND KETONES 3 One cubic centimeter (1 cm 2) of KOH solution (1 g KOH + 6 cm 3 water) was slowly added to the mixture of selected aidehyde 1 (0.25 mole) and aliphatic carbonyl com- ponent (propanal, butanal, or 2-butanone, 0.35 mole), with intense cooling of the reactor. After the first exothermic reaction period, the remaining part of the KOH solution was slowly added to the reaction mixture. The temperature was kept under 30øC. The reaction medium was stirred for one hour at 30øC. After that time, water (50 cm 3) was added, and phase separation followed. The aqueous phase was extracted with toluene (2 x 50 cm•). The toluene solution was washed to a neutral pH value. The solvent was evaporated and the crude product was distilled under vacuum.

496 JOURNAL OF COSMETIC SCIENCE Table I Odor Characteristic of New Furan Compounds Compound Odor characteristic //•••L•oH /•••V•• 0 H 4a 4b 4c 5a 5b 7a Intense, floral, with a note of lupine Less intense, floral, with a note of cloves Intense, floral, with a note of tomato leaves Intense, floral-vegetable Intense, mushroom-floral Intense, floral-mushroom /•.•,,•OH /•OH 7b 8a 8b Intense, floral, with a woody note Intense, floral, with a note of lupine Intense, floral, with a note of tomato leaves GENERAL PROCEDURE FOR PREPARATION OF ALCOHOLS 4, 5, AND 7 The selected aidehyde (0.45 mole) was dissolved in methanol (200 cm 3) with continuous stirring, and then the solution of NaBH 4 (4 g) in 10% NaOH (80 cm 3) was added dropwise with cooling. The reaction medium was stirred for one hour at 40ø-50øC. After evaporation of the major part of the methanol, water (50 cm 3) was added and phase separation followed. The aqueous phase was extracted with toluene (2 x 50 cm3). The toluene solution was washed to a neutral pH value. After evaporation of the toluene, the crude product was distilled under vacuum. GENERAL PROCEDURE FOR PREPARATION OF ALDEHYDES 6 Two grams (2 g) of Pd on activated carbon were added to the solution of aidehyde 3 (0.15 mole) in cyclohexene (200 cm 3) and refluxed for 20 hours. TLC confirmed full