&agr;-Oxygen-substituted cyclohexane propionitriles,...

Details &agr;-Oxygen-substituted cyclohexane propionitriles,... &agr;-Oxygen-substituted cyclohexane propionitriles,...

2000-03-02

2001-10-30

Warden, Jill (Department: 1743)

Perfume compositions

Perfume compositions

Cyano containing active ingredient

C512S025000, C558S430000, C558S357000, C558S371000

Reexamination Certificate

active

06310032

ABSTRACT:

BACKGROUND OF THE INVENTION
Our invention relates to &agr;-oxygen-substituted cyclohexane propionitriles defined according to the structure:
wherein R
20
and R
21
are the same or different C
1
-C
4
lower alkoxy; or wherein R
20
is hydrogen and R
21
is hydroxy, C
1
-C
3
lower alkoxy or C
1
-C
3
lower acyloxy, processes for preparing same and perfumery uses thereof; and wherein R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
are the same or different hydrogen or C
1
-C
4
lower alkyl.
Woody, orris, sweet, coumarinic aromas with spicy and soft 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).
Nitriles such as citronellyl nitrile have been known for use in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes for a number of years.
Nothing in the prior art, however, discloses the &agr;-oxygen-substituted cyclohexane propionitriles of our invention for their organoleptic utilities.
is known for use in perfumery as disclosed in Japanese Published Application No. JP60/151440 (Sumitomo). The synthesis of this material is also disclosed by Cotarca, et al,
SYNTHESIS,
1996, pages 328-332.
The nitrile having the structure:
is disclosed in the prior art, but not for its perfumery uses by Dynamit Nobel AG in German Patent No. 1,912,790 (1970). Its preparation is set forth by Duféÿ,
BULLETIN DE LA SOCIÉTÉ CHIMIQUE DE FRANCE,
1968, No. 11.
The compounds having the structure:
wherein R
11
is methyl or ethyl are disclosed by Giese, et al,
Chem. Ber.,
117 (1984) 6, pages 2120-2139, but their organoleptic utilities are not disclosed.
The compound having the structure:
The compound having the structure:
is disclosed by Ture{haeck over (c)}ek, Collection Czechoslovak Chem. Commun. (1982), Vol. 47 (3), pages 858-876, but its organoleptic uses are not disclosed or inferred.
Nothing in the prior art discloses any organoleptic uses of the compounds having the structure:
wherein R
20
and R
21
are the same or different C
1
-C
4
lower alkoxy; or wherein R
20
is hydrogen and R
21
is hydroxy, C
1
-C
3
lower alkoxy or C
1
-C
3
lower acyloxy; and wherein R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
are the same or different hydrogen or C
1
-C
4
lower alkly.
Furthermore, the prior art does not disclose the compounds having the structure:
wherein R
9
and R
10
are C
1
-C
4
lower alkyl.


REFERENCES:
patent: 3816503 (1974-06-01), van Poelvoorde
patent: 4219449 (1980-08-01), Lenselink
patent: 5011970 (1991-04-01), Lenselink
patent: 5292902 (1994-03-01), Helmlinger
patent: 5917067 (1999-06-01), Cotarca et al.
patent: 60152440 (1985-08-01), None
Stork and Zhao,Tetrahedron Letters, vol. 30, No. 3, pp. 287-290 (1989) entitled “A Simple Method of Dethioacetalization”.
Giese, et al,Chem. Ber., 117, pp. 2132-2139 (1984) (publication receipt date Aug. 17, 1983) entitled “Diastereoselektivität der CC-Verknüpfung cyclischer Radikale”.
Duféÿ,Bulletin De La Sociét{acute over (e )}Chimique De France, 1968, No. 11, pp. 4653-4662 (manuscript received Nov. 22, 1967) entitled “Sur la préparation des alcoylhexahydrochromannols-2”.
Ture{haeck over (c)}ek,Collection Czechoslovak Chem. Commun.[vol. 47], 1982, pp. 858-876 and entitled “Preparation of 7-Oxabicyclo[4.3.0]Nonanes and 2-Oxabicyclo[4.4.0]Decanes Specifically Labelled with Deuterium”.

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