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The following Examples will serve to illustrate certain specific embodiments within the scope of aroma chemicals and are not to be construed as limiting the scope thereof.
EXAMPLE I
aroma chemicals4,4,6-trimethylbicyclo[4.2.0]octane-2-ol
To a 2-liter 3-necked flask fitted with a mechanical stirrer, additional funnel, reflux condenser and drying tube was added 15 g. (0.39 mole) of sodium borohydride and 500 ml. 2-propanol. To this solution was slowly added 218.6 g. (1.317 moles) of 4,4,6-trimethylbicyclo[4.2.0]octane-2-one in 50 ml. of 2-propanol. After 2 hours, about 200 ml. of water was added. The mixture was stirred an additional 1 hour, then about 35 ml. concentrated hydrochloric acid was added. After another 1 hour of stirring, 400 ml. of toluene and 500 ml. of water were added. The layers were separated and the organic layer was washed three times with 100 ml. of water. The combined water layers were extracted with toluene. The toluene layers were combined and dried over potassium carbonate. The solution was concentrated in vacuo and the residue distilled through a 25 cm. Vigreux--column to yield 215.8 g. (1.284 moles, 97.5 % yield) of 4,4,6-trimethylbicyclo [4.2.0]octane-2-ol. IR: 3360 cm -1 .
EXAMPLE II
aroma chemicalstricyclo[8.4.0.0 2 ,9 ]tetradecane-11-ol
To a solution of 2.06 g. (0.01 mole) of the tricyclo ketone in 100 ml. of 2-propanol in a 250 ml. Erlenmeyer flask equipped with magnetic stirring bar was added 0.57 g. (0.015 mole) of sodium borohydride. The reaction mixture was stirred overnight. The mixture was transferred to a separatory funnel, a few drops of concentrated hydrochloric acid added, and then extracted with three 100 ml. portions of ether. The combined ether extracts were washed with three 25 ml. portions of 10% aqueous sodium bicarbonate solution, dried over magnesium sulfate and concentrated in vacuo to yield a white crystalline solid that was recrystallized from petroleum ether to yield 1.20 g. (0.0058 mole, 58% yield) of tricyclo[8.4.0.0 2 ,9 ]tetradecane-11-ol. m.p.: 141.5° - 142.0° C. IR: 3610 cm -1 , 3450 cm -1
EXAMPLE III
The characteristic aroma chemicalss of some of the compounds of the instant invention are as follows:
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Compound of Example Aroma chemicals
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i camphor, minty, woody, patchouly
II weak to odorless, woody
III sandalwood
IV camphoraceous, musty, sweet
(extremely)
VI sweet, powdery, weak, fairly
lasting
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While the invention has been described herein with regard to certain specific embodiments, it is not so limited. It is to be understood that variations and modifications thereof may be made by those skilled in the art without departing from the spirit and scope of the invention.
