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

NEW FRAGRANCES FROM 2-METHYLFURAN: I 95 Table I (continued) Lp. Compound Odor characteristic 15 16 OAc /OAc 9b Floral, with a strong note of green peas 9c Fruity, vegetable-like toluene solution obtained was washed to a neutral pH value. After evaporation of toluene, the crude product was distilled under vacuum. GENERAL PROCEDURE FOR THE PREPARATION OF ESTERS 6a-f The selected alcohol (0.2 mole), acetic or propionic anhydride (0.22 mole), and anhy- drous sodium acetate (2 g) were placed in a flask equipped with a thermometer and mechanical stirrer. The reaction mixture was stirred and heated to 90øC. Mixing was continued for another hour. The product was cooled down, and then water (50 cm 3) was added followed by phase separation. The aqueous phase was extracted with toluene (2 x 50 cm3). The toluene solution obtained was washed to a neutral pH value. After evaporation of toluene, the crude product was distilled under vacuum. GENERAL PROCEDURE FOR THE PREPARATION OF ACETALS 7a-c The selected alcohol (0.2 mole), ethylvinyl ether (0.25 mole), and few a crystals of p-toluenesuphonic acid were placed in a flask equipped with a thermometer and me- chanical stirrer. The reaction mixture was stirred vigorously and cooled down. When the exotermic effect stopped, the mixture was stirred for one hour at room temperature. Then water (50 cm •) was added and phase separation followed. The aqueous phase was extracted with toluene (50 cm•). The toluene solution obtained was washed to a neutral pH value. After evaporation of toluene, the crude product was distilled under vacuum. GENERAL PROCEDURE FOR PREPARATION OF ALCOHOLS 8 Placed in a three-necked flask were 7.2 g (0.3 mole) of dry magnesium wire, 45 g (0.6 mole) of THF-dried over molecular sieves 4A, and 150 ccm of dry toluene. Reaction was initiated by introducing 5g of methyl iodide. The remaining portion of methyl iodide (0.3 tool) in toluene (50 cm •) was added dropwise over one hour. The temperature was maintained between 35 ø and 40øC with cooling. Then 45.5 g (0.3 mole) of aldehyde 4 in toluene (50 cm •) was added dropwise over 30 min. Hydrolysis was carried out by means of 20% wt of aqueous acetic acid (100 cm3). Phases was separated. The aqueous