8-EXO-FORMYL-2,6-EXO-TRICYCLO 5.2.1.0?2,6 DECANE, METHOD FOR PREPARING IT AND USE OF SAME

摘要

It has been discovered that 8-exo-formyl-2,6-exo-tricyclo [5.2.1.02,6] decane having the constitution and stereochemistry of formula (I) has particularly useful olfactory properties which are clearly superior to those 8-endo-epimers and which already make themselves felt if the compound (I) is enriched with mixtures of 8-exo / endo-epimers. Compound (I) can therefore be used advantageously, in pure or enriched form, as an odorous material or as a constituent of perfume compositions. To make an enriched epimer mixture, a mixture obtained in a known manner (US-PS 3 270 061) and having an exo / endo ratio of 1.45: 1 is brought into equilibrium by basic catalysis, preferably by action. of alkali hydroxides in an alcoholic solution, to give an exo / endo ratio of 5.25: 1. Alternatively, the enriched epimer mixture can be prepared from 8-formyl-2,6-exo-tricyclo [5.2.1.02,6] decene-3 (4), subjected to catalytic hydrogenation, for example with charcoal palladous and then eventually brought into balance. Or 2,6-exo-tricyclo [5.2.1.02,6] decene-8 can be hydroformylated and possibly still brought into equilibrium. To prepare the pure compound (I), preferably a mixture of 8-exo / endo-epimers obtained in a manner known per se is reduced to a corresponding alcohol mixture, from which the methylol with 8-exo configuration is isolated by chromatography or distillation and oxidized to again obtain the aldehyde (compound I).