Aromatic compounds and their use in perfumery

Details Aromatic compounds and their use in perfumery Aromatic compounds and their use in perfumery

1995-01-13

1996-06-18

Reamer, James H.

Perfume compositions

Perfume compositions

Ring containing active ingredient

512 20, 568425, 568435, 568592, 568315, 549355, 75217411, 752 86, 474 764, A61K 746

Patent

active

055277691

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to novel aromatic acetals and aldehydes which are useful as perfuming ingredients. It concerns, in fact, compounds of formula ##STR3## wherein symbol X represents a group --CHO or an acetal group of formula ##STR4## symbols R', taken separately, represent each a C.sub.1 to C.sub.4, linear or branched, saturated or unsaturated, alkyl radical or, taken together, represent a C.sub.1 to C.sub.4 alkylene radical, which may be substituted, and symbol R represents a hydrogen atom or a methyl radical.


PRIOR ART

As is apparent from the following table, several compounds having a structure close to that of compounds (I) are known from the prior art, some of which have met with commercial success. Furthermore, several of these compounds are described in the textbook of S. Arctander, Perfume and Flavor Chemicals, Montclair, N.J., USA (1969), as is indicated in the table.


TABLE __________________________________________________________________________ Compounds Odor Reference __________________________________________________________________________ ##STR5## very strong, floral lily of the valley Naarden Int.- product sheet ##STR6## floral, green, lime-blossom Arctander 496 ##STR7## floral, green, cucumber, melon, lime-blossom Arctander 758 ##STR8## floral, sweet, green, fruity Arctander 2741 ##STR9## floral, sweet, spicy Arctander 2073 ##STR10## floral, green, lily of the valley NL 7905175 __________________________________________________________________________
In spite of the abundance of known products of this type, the research activity in this field remains intense, namely with the aim of finding compounds which present a greater variety of odor nuances and also compounds whose stability in composition is improved over that of the known products. In fact, these known aldehydes are very sensitive to oxidation, being easily converted to their corresponding acids, which are either odorless or have unpleasant fragrances, but, in any case, do not possess any longer the desired odor characters.


DESCRIPTION OF THE INVENTION

We have now surprisingly discovered that compounds (I) possess very useful odor properties, which are also distinct from those of the prior art products. In particular, we have observed that 3-(4-tert-butyl-2-methyl-1-phenyl)propanal according to the invention is capable of replacing advantageously, in its typical applications, p-tert-butyl-.alpha.-methyl-hydrocinnamic aldehyde or 3-(4-tert-butyl-1-phenyl)-2-methyl-propanal, also known under the tradename of LILIAL.RTM. (origin: Givaudan-Roure, Vernier, Switzerland), while being, in practice, of a wider use than the latter.
This result of our researches was totally unexpected since, despite the large number of novel compounds prepared by us and possessing alkyl or alkenyl groups in the different positions of the benzene ring and of the side chain, only compounds (I), and in particular the derivative wherein R=H, have shown exceptional odor characters. The latter became in fact evident as a result of laborious olfactive evaluations carried out by panels of expert perfumers, who surprisingly discovered the superior odor quality of these compounds, which was apparent not only upon the evaluation on smelling strip of the compound in a pure state or in composition, but also upon its use for perfuming namely detergents and fabric softeners.
Thus, it has been ascertained that 3-(4-tert-butyl-2-methyl-1-phenyl)propanal, the preferred compound of the invention, develops an odor which is reminiscent of that of the known aldehyde cited above, but which in addition possesses a perfectly distinct anisic, lily of the valley character.
Furthermore, as is apparent from the examples presented further on, this compound according to the invention, relative to the above-cited known aldehyde, possesses an enhanced odor strength and better stability against oxidation. Thus, the invention provides a compound which is more stable than known LILIAL.RTM. and which is as convenient for use in

REFERENCES:
patent: 3372199 (1968-03-01), Rylander et al.
patent: 3548006 (1970-12-01), Scriabine
patent: 3879425 (1975-04-01), Hall et al.
patent: 4486607 (1984-12-01), Webb
patent: 4512918 (1985-04-01), Wiegers et al.
patent: 5086038 (1992-02-01), Naef et al.
Cagniant P. et al., "Cleavage and Migration of Tert-butyl Groups in Friedel-Crafts Reactions. I. Synthesis of tert-butyl-substituted tetralones"; College Science University Metz; Metz; France; BSCFAS 1969, No. 3; pp. 985-91.
Rieche A. et al., "Die Darstellung von Homoisochroman.sup.2 "; Rieche and Gross, 1962, pp. 91-95.
von der Bruggen et al., "Relative Reactivities of Acetals and Orthoesters in Lewis Acid Catalyzed Reactions with Vinyl Ethers. A Systematic Investigation of the Synthetic Potential of Acetals and Orthoesters in Electrophilic Alkoxyalkylations of Enol Ethers"; J. Org. Chem. 1988, 53, pp. 2920-2925.

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