1,2,3,3,5,6,-Hexamethyl-bicyclo(2.2.2)-oct-5-en-2-ol, process for producing same, intermediates useful in said process and organoleptic uses of same

Described is 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol as a mixture of isomers and in its isomeric forms having the structures: and the uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles, and colognes. Also described is a novel process for preparing 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol by first reacting the compound having the structure: with the compound having the structure: in order to produce the ketone defined according to the structure: which is hydrogenated to form the compound having the structure: and further hydrogenated to form the ketone having the structure: This ketone is reacted with CH3M wherein M represents Li or MgX and wherein X is chloro, bromo or iodo to form the organometallic intermediate defined according to the structures: These compounds are then hydrolyzed with dilute acid to form the organoleptically useful 1,2,3,3,5,6-hexamethylbicyclo[2.2.2]oct-5-en-2-ol isomers of our invention defined according to the structures: >