The compounds of formula EQU X--CH.sub.2 --CH(OH)--CH.sub.2 --R (I) wherein symbol R represents a C.sub.1 -C.sub.3 alkyl radical and X a substituted cyclohexyloxy group of formula ##STR1## wherein index n stands for zero or one, the dashed lines indicate a single bond (n=1) or a double bond in position 2 (n=0) or 3 (n=1) and each of symbols R.sup.1 to R.sup.6 designates a hydrogen atom or a methyl radical, are new and can be conveniently utilized as perfuming and flavoring ingredients. They develop in particular woody-ambery notes.

BRIEF SUMMARY OF THE INVENTION 
The instant invention relates to novel compounds of formula 
EQU X--CH.sub.2 --CH(OH)--CH.sub.2 --R (I) 
wherein symbol R represents a C.sub.1 -C.sub.3 alkyl radical and X a 
substituted cyclohexyloxy group of formula 
##STR2## 
wherein index n stands for zero or one, the dashed lines indicate a single 
bond (n=1) or a double bond in position 2 (n=0) or 3 (n=1) and each of 
symbols R.sup.1 to R.sup.6 designates a hydrogen atom or a methyl radical. 
This invention relates also to a process for the preparation of compounds 
(I) which process makes use as starting materials of the compounds of 
formula (IV) 
##STR3## 
wherein the dashed lines, index n and symbols R.sup.1 to R.sup.6 have above 
given meaning, and of formula 
##STR4## 
wherein R represents a C.sub.1 to C.sub.3 alkyl radical. 
The present invention provides further a perfuming or a flavoring 
composition containing as active ingredient a compound of formula (I). 
This invention provides further a perfumed product or a foodstuff, a 
beverage, a pharmaceutical preparation or a tobacco product containing as 
active perfuming or flavoring ingredient a compound of formula (I). 
BACKGROUND OF THE INVENTION 
Certainly, one of the most widely examined class of odorants is represented 
by the woody compounds. This class consists of chemicals of very different 
nature and includes alcohols, esters, ketones and ethers having mono- or 
polycyclic structure, as well as macrocyclic derivatives. Among the woody 
odorants possessing an alicyclic structure, one may cite the aliphatic 
ether derivative of ionones, such as for example the compounds of formula 
##STR5## 
which develop an overall woody odor accompanied by a fruity, ambery or, in 
certain instances, tobacco-like tonality (see DE-OS No. 2,827,636). 
Several methyl homologs of .beta.-ionone are disclosed by S. Arctander in 
Perfume and Flavor Chemicals (Montclair, N.J. 1969, sections 2087 and 
2088). 
Alicyclic alcohol of formula 
##STR6## 
is known to possess fixative properties in perfumes and it develops an 
odor of woody-ambery type (see DE-OS No. 2,807,584). 
Strange as it may seem, an analogous class of compounds has remained so far 
unrecognized. We have now discovered that oxygenated alicyclic derivatives 
of formula (I) develop useful organoleptic properties and that 
consequently they can be used as valuable ingredients in the perfume and 
the flavor industry. 
PREFERRED EMBODIMENTS OF THE INVENTION 
In the field of fragrances, compounds (I) are characterized by an elegant, 
warm and clinging woody-ambery scent enriched by a slightly animal 
tonality reminiscent of natural amber; in some instances, their odor can 
also be fruity or flowery. Compounds (I) are powerful and show medium 
tenacity. They are especially suitable for manufacturing fragrance 
compositions of various nature, such as for instance chypre, rosy, woody 
or fougere type compositions, to which they confer harmony and richness 
without however destroying the desired balance of their woody-ambery 
tonality. 
Compounds (I) can be utilized successfully for the manufacture or perfumed 
products such as soaps, detergents, household materials and cosmetics, 
namely cosmetics for men-lines such as colognes or after-shave lotions. 
The proportions necessary to achieve the desired effects can vary within a 
wide range of values. The experts in the art realize that those values 
depend on the nature of the coingredients used in a given composition and 
on the nature of the products to which they are added. Typically, 
concentrations of the order of 1 to 25%, or even 30% by weight in the case 
of perfume bases or concentrates, can be used. 
In the field of flavors, compounds of formula (I) are characterized by a 
taste and an aroma which may be defined as being woody and ambery. Due to 
their gustative properties, compounds (I) are particularly adapted to the 
aromatization of tobacco or tobacco products. They can be used to confer 
the typical aroma character of oriental tobacco blends. 
The compounds of the invention, or the compositions containing them, may be 
used in a variety of forms, but they are preferably used in solution. The 
form in which a given compound is best employed will depend upon its 
chemical nature, solubility and stability. Flavoring can occur in any step 
of the manufacturing process. In tobacco aromatization for instance, the 
flavor can be added at any step of tobacco treatment during aging, drying 
or curing before actual cigarettes manufacture. A convenient method for 
flavoring tobacco consists in spraying it with an alcoholic solution of 
the compound or flavoring composition. As an alternative to alcohol, a 
mixed solvent may be used for this purpose, such as a mixture of alcohol 
and propylene glycol. 
The proportions in which the flavoring agent of the invention are used can 
vary widely, depending upon the type of product to which they are added 
and the specific organoleptic effect it is desired to achieve. For 
example, interesting flavoring effects can be achieved with amounts 
ranging from 1 to 100 ppm (parts by weight per million), based on the 
weight of the product flavored. Typically, proportions from 5 to 10 ppm 
are preferred; but in all cases, these ranges can be varied in order to 
achieve specific effects. 
According to the invention, the compounds of formula (I) can be prepared 
from alicyclic alcohols of formula 
##STR7## 
wherein symbols R.sup.1 to R.sup.6, index n and the dashed lines are 
defined as indicated above for formula (I), by reacting them with a 
compound of formula 
##STR8## 
wherein symbol R represents a C.sub.1 to C.sub.3 alkyl radical. 
According to the process of the invention, the reaction is carried out in 
the presence of a strong base such as an alkali metal hydride, for example 
sodium or lithium hydride, or an alkali metal, for example sodium. 
Moreover, the reaction is effected in the presence of an inert organic 
solvent such as an ether or an aliphatic or aromatic hydrocarbon, e.g. 
petrol ether or toluene (see in this respect: Houben-Weyl, Methoden der 
Organischen Chemie, Georg Thieme Verlag, Stuttgart 1965, Vol. VI/3). 
Alicyclic alcohols of formula (IV) used as starting materials for the 
process of the invention are either commercial products or, in the 
alternative, they can be prepared by reducing the corresponding available 
ketones according to current techniques. 
Compounds (I), as directly obtained by the process of the invention, occur 
in various stereoisomeric form according to the nature of the different 
substituents on the six-membered ring. The different isomers may be 
seperated by means of the usual techniques, for instance by preparative 
vapour phase chromatography. Though characterized by their main typical 
woody-ambery smell, different isomers possess different odor nuances. For 
all practical purposes however, it is preferred to use the mixture of 
isomers as directly obtained by the above described process.