Perfume compositions – Perfume compositions – Ring containing active ingredient
Reexamination Certificate
2000-10-11
2001-08-07
Richter, Johann (Department: 1621)
Perfume compositions
Perfume compositions
Ring containing active ingredient
C512S017000, C512S019000, C568S444000, C568S445000, C568S446000, C510S101000
Reexamination Certificate
active
06271193
ABSTRACT:
BACKGROUND OF THE INVENTION
Our invention relates to pentamethyl indane derivatives, all derived from the hydrocarbon having the structure:
by means of first reacting such hydrocarbon with a mixture of carbon monoxide and hydrogen using an “oxo reaction catalyst” in order to form a carboxaldehyde having the structure:
or stereoisomers thereof. Such carboxaldehydes may then be used as is for their perfumery properties or may be reacted further, for example, by means of reduction, Grignard synthesis or the like. The resultant carboxaldehydes and resultant derivatives thereof have intense and substantive and aesthetically pleasing fragrance nuances and are thus useful in the formulation of fragrance compositions.
Velvety, diffusive, sweet, rich, warm, sensual, intense musky, floral, ambery, spicy, woody, balsamic, earthy, rooty and vetiver-like aromas with sensual, animalic, powdery, creamy, costus and musky topnotes and sweet, musky, spicy and floral undertones are particularly desirable in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, hair preparations, cosmetic powders and perfumed polymers).
Compounds having the oxygen-substituted pentamethyl indane structure and pentamethyl indane hydrocarbons are known for use in perfumery. Thus, U.S. Pat. No. 3,806,472 issued on Apr. 23, 1974 discloses the use in prefumery of the compound having the structure:
U.S. Pat. No. 3,636,165 issued on Jan. 18, 1972 discloses the perfumery utilities of the compounds having the structures:
U.S. Pat. No. 3,773,836 issued on Nov. 20, 1973 discloses the perfumery use of the compound having the structure:
U.S. Pat. No. 4,902,840 issued on Feb. 26, 1990 discloses the perfumery use of the compound having the structure:
The prior art does not, however, disclose the organoleptic utilities of compounds defined according to the structure:
wherein G′ is one of the moieties:
wherein R
6
and R
7
are the same or different C
1
-C
3
lower alkyl and R
1
, R
2
, R
4
and R
5
are the same or different methyl or ethyl; and R
3
is hydrogen or methyl with the provisos:
(i) when R
3
is hydrogen, one of R
1
, R
2
, R
3
and R
4
is ethyl and the other of R
1
, R
2
, R
3
and R
4
is methyl; and
(ii) when R
3
is methyl, then R
1
, R
2
, R
3
and R
4
are each methyl.
THE INVENTION
Our invention is directed to carbon containing, functional group substituted 4,5,6,7-tetrahydro-polyalkylated-4-indanes,isomers thereof and processes for preparing same, which substituted indanes are defined according to the structure:
wherein G is one of the moieties:
and wherein and R
1
, R
2
, R
4
and R
5
are the same or different methyl or ethyl; and R
3
is hydrogen or methyl with the provisos that:
(i) when R
3
is hydrogen, one of R
1
, R
2
, R
4
and R
5
is ethyl and the other is methyl; and
(ii) when R
3
is methyl, then one of R
1
, R
2
, R
4
and R
5
is methyl; wherein R
6
and R
7
are the same or different C
1
-C
3
lower alkyl; and wherein X is chloro, bromo or iodo.
Our invention is also directed to the use of 4,5,6,7-tetrahydro-polyalkylated-4-indane carbinols, carbinyl esters, carboxaldehydes, ketones and cyanides as fragrance ingredients for use in imparting, augmenting or enhancing the aroma of perfume compositions, colognes, perfumed articles and perfumed polymers. Such 4,5,6,7-tetrahydro-polyalkylated-4-indane carbinols, carbinyl esters, carboxaldehydes, ketones and cyanides are defined according to the generic structure:
wherein G′ is one of the moieties:
and wherein and R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
are defined, supra.
The 4,5,6,7-tetrahydro-polyalkylated-4-indane carbinols, carbinyl esters, carboxaldehydes, ketones and cyanides have velvety, diffuse, sweet, rich, warm, sensual, intense musky, floral, ambery, spicy, woody, balsamic, earthy, rooty and vetiver-like aromas with sensual, animalic, powdery, creamy, costus and musky topnotes and sweet, musky, spicy and floral undertones and impart, augment or enhance such properties to perfume compositions, colognes, perfumed articles and perfumed polymers.
Specific examples of the 4,5,6,7-tetrahydro-polyalkylated-4-indane carbinols, carbinyl esters, carboxaldehydes, ketones and cyanides of our invention have the following structures:
The products of our invention may exist as “cis” or “trans” stereoisomers or “cis” or “trans” racemic mixtures, for example, the materials having the structures:
or the compounds having the structures:
In producing the 4,5,6,7-tetrahydro-polyalkylated-4-indane carbinols, carbinyl esters, carboxaldehydes, ketones and cyanides of our invention, the starting materials are the hydrocarbons defined according to one or a mixture of the following structures:
generically shown as the material having the structure:
wherein R
1
, R
2
, R
4
and R
5
are the same or different methyl or ethyl and R
3
is hydrogen or methyl with the provisos:
(i) when R
3
is hydrogen, one of R
1
, R
2
, R
4
and R
5
is ethyl and the other is methyl; and
(ii) when R
3
is methyl, one of R
1
, R
2
, R
4
and R
5
are each methyl.
The aforementioned hydrocarbons may be prepared by means of dehydrohalogenation or dehydration of such compounds having the generic structure:
wherein X is chloro, bromo or hydroxy under conditions well known to those having ordinary skill in the art, or more specifically, dehydrohalogenation of, for example, the compound having the structure:
according to the reactions:
wherein D is a dehydrohalogenating agent; D′ is a dehydrohalogenating agent or a dehydrating agent; and D″ is a dehydrating agent.
The generic dehydrating reaction is shown thusly:
The cyclohexenol reactant is prepared by reduction of the corresponding ketone according to the reaction:
under conditions well known to those having ordinary skill in the art.
Thus, for example, a compound having the structure:
is shown to be synthesized in U.S. Pat. No. 3,806,472 issued on Apr. 23, 1974, the specification for which is incorporated by reference herein.
The compounds having the structures:
are shown to be produced in U.S. Pat. No. 3,636,165, the specification for which is incorporated by reference herein.
The compound having the structure:
is shown to be produced according to U.S. Pat. No. 3,773,836 issued on Nov. 20, 1973, the specification for which is incorporated by reference herein.
The compound having the structure:
an isomer or adjacent methyl homologue of a member of the group of 4,5,6,7-tetrahydro-polyalkylated-4-indane carbinols, carbinyl esters, carboxaldehydes, ketones and cyanides of our invention is shown to be produced according to U.S. Pat. No. 4,902,840 issued on Feb. 26, 1990, the specification for which is incorporated by reference herein.
The hydrocarbons having the structure:
according to the processes of our invention, are then reacted with a mixture of carbon monoxide and hydrogen according to the reaction:
under “oxo” reaction conditions using an “oxo” reaction catalyst.
Depending upon the oxo reaction catalyst, either racemic mixtures can be formed or mixtures having a preponderance of a particular stereoisomer, are formed, for example, one of the materials having the structure:
or racemic mixtures or stereoisomers of compounds having the structure:
having, for example, an enantiomeric excess percent of greater than 50%, [EE%>50%].
When using an oxo reaction catalyst that will give rise to a mixture having a positive or negative optical rotation, that is a mixture of stereoisomers having an enantiomeric excess percent of greater than 50%, [EE%>50%], such oxo reaction catalysts as are set forth in Published European Application No. EP0 877,029 A2 published on Nov. 11, 1998 may be used (the specification for which is incorporated by reference herein), having for example, the structure:
wherein Ar and Ar′ represent aerial groups and wherein R
1
″, R
2
″ and R
3
″ repr
Beck Charles E. J.
Hanna Marie R.
Heinsohn Jr. Howard H.
Levorse, Jr. Anthony T.
Sprecker Mark A.
International Flavors & Fragrances Inc.
Leightner Joseph F.
Richter Johann
Witherspoon Sikarl A.
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