8-exo-formyl-2,6-exo-tricyclo(5.2.1.02,6)decane, method of prepa

Perfume compositions – Perfume compositions – Ring containing active ingredient

Patent

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Details

568445, 568443, 568444, A61K 746

Patent

active

054928877

DESCRIPTION:

BRIEF SUMMARY
This appln. is a PCT of 371 of DE92/00,307 filed Apr. 10, 1992, pending.
In modern industrial perfumery there ms a permanent demand for new scent products having, in addition to high stability and hence varied technical possible applications, scent notes that are as original and aesthetic as possible. An additional factor in the industrial production of scents is the provision of such new scents which, starting from synthetic raw materials, are available in large quantities and cheaply.
The present invention relates to 8-exo-formyl-2,6-exo-tricyclo[5.2.1.0.sup.2,6 ]decane (1) which is a valuable new scent either in its pure form or in an enriched form together with its 8-endo-isomer 2. ##STR1##
It is novel that the aldehyde 1 having the constitution and stereochemistry shown not only results in particularly positive scent characteristics but also that it is of particular industrial value owing to its behavior in perfume-technical applications. The compound 1 having the constitution shown and the analogous configuration has not yet been described.
C-8-substituted tricyclo[5.2.1.0.sup.2,6 ]decane-derivatives without a statement relating to the stereochemistry at position C-8 are described in U.S. Pat. No. 3,270,061 (Aug. 30, 1966). Among those is also the 8-formyl compound D which, however, is not mentioned in the claims of the above mentioned patent. ##STR2##
In this description, the stereochemistry of the ring system is described as 2,6-exo. However, this is not considered as being relevant for the scent characteristics of the mentioned or claimed compounds. In the above mentioned patent in column 1, lines 69 to 72 there is a statement that the compounds described usually and preferably consist of the 2,6-exo-isomers and that the corresponding endo-isomers could, however, be used in the same way in accordance with the invention therein. There is also no statement about the possible importance of the C-8 stereochemistry. It is therefore novel and surprising that the aldehyde 1, meaning exclusively the 2,6 exo-configuration, with the exo-configuration of the formyl group at the C-8, provides a scent which is characterised by a particularly natural and aesthetically valuable green note.
For the aldehyde D of the same constitution which has been obtained in accordance with the U.S. Pat. No. 3,270,061 an intensive green note having earthy top-notes is mentioned (column 5, lines 69 to 71). In this patent specification, it is also stated that the aldehyde D is of value for the formulation of heavy flowery notes, such as violet notes. However, in the U.S. patent, aldehyde D has not been claimed as a scent. In contrast, only ketones E which are produced by consecutive reactions have been claimed and their scent characteristics have been extensively described. One can presume that owing to its earthy bynote aldehyde D was only of a limited value and hence has not found entry into the international perfumery.
The aldehyde D can be produced by analogy to U.S. Pat. No. 3,270,061 from the tricyclic ketone A (TCD-ketone A, commercial product of the firm Hoechst, Germany): by conversion with ethyl chloro-acetate in the presence of sodium hydride the glycidic ester B is obtained; the saponification of B results in the glycidic acid C which also could be converted into the aldehyde D by heating with potassium acetate. By reproducing the prescription given in U.S. Pat. No. 3,270,061 we obtained the aldehyde D at a purity of about 99% (Example 1). The known scent characteristics could be confirmed by us. Surprisingly, we have now found that under the effect of acids or bases, preferably of alkaline hydroxides or alkaline carbonates in an alcoholic solution, a clear improvement of the scent of aldehyde D can be noticed. The scent of the treated material is not only clearly stronger, but also more naturally green. ##STR3##
The analysis of the aldehyde D produced analogously to U.S. Pat. No. 3,270,061 for the presence of other compounds after the treatment with acids or bases is difficult even using modern analytical methods. Th

REFERENCES:
patent: 3270061 (1966-08-01), Chodroff et al.
patent: 4225515 (1980-09-01), Weber et al.
patent: 4229324 (1980-10-01), Takaishi et al.
patent: 4319049 (1982-03-01), Rogier
patent: 4541949 (1985-09-01), Sprecker et al.
patent: 4762819 (1988-08-01), Brunke
European Patent Office Search Report, dated Jun. 20, 1992, by Examiner J. C. Henry.

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