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

SYNTHESIS OF FRAGRANCES FROM 2-METHYLFURAN 497