Isolongifolenyl ethers, their preparation and their use

Abstract

Cyclic isolongifolenyl ethers of the general formula A, where wavy lines mean α- and β-configuration, and R is the following radicals. R=Me, Et, Pr, iso-Pr, Bu, sec-Bu, iso-Bu, tert-Bu. These isolongifolenyl ethers are excellent fragrances and can, in particular, be used as a constituent of fragrance mixtures or perfume oil for the perfuming of cosmetic or technical consumer goods. Also described are processes for the preparation of said cyclic isolongifolenyl ethers.

What is claimed is:  
     
         1 . A cyclic isolongifolenyl ether of the general formula A:  
       
         
           
           
               
               
           
         
       
       where wavy lines mean α- as well as β-configuration, and R is the following radicals: 
 R=Me, Et, Pr, iso-Pr, Bu, sec-Bu, iso-Bu, tert-Bu  
 
     
     
         2 . The cyclic isolongifolenyl ether as claimed in  claim 1 , wherein the hydrogen at the bridgehead of the two five-membered rings is α-configured.  
     
     
         3 . The cyclic isolongifolenyl ether as claimed in  claim 1 , wherein R=Me, Et, Pr or iso-Pr, where the configuration of the ether functions is α or β, or the cyclic isolongifolenyl ether comprises a mixture of enantiomers which differ in their configuration of the ether function.  
     
     
         4 . The cyclic isolongifolenyl ether as claimed in  claim 1 , wherein R=Me, where the configuration of the methyl ether function is α or β, or the cylic isolongifolenyl methyl ether comprises a mixture of enantiomers which differ in the configuration of the methyl ether function.  
     
     
         5 . A process for the preparation of a cyclic isolongifolenyl ether as claimed in  claim 1 , comprising reacting isolongifolenol in enantiomerically pure form or as enantiomer mixture either under acid-catalyzed conditions with an aliphatic alcohol (alkyl hydroxide), or under base-catalyzed conditions with an alkyl halide or alkyl sulfate in an aprotic solvent, the alkyl function in question corresponding to the radical R of the cyclic isolongifolenyl ether.  
     
     
         6 . A method for modifying the fragrance of a cometic composition, a laundry detergent composition, a household cleaning composition or a personal hygiene composition, the method comprising adding to said composition a fragrance mixture or perfume oil comprising as a fragrance or constituent a cyclic isolongifolenyl ether of the general formula A:  
       
         
           
           
               
               
           
         
       
       where wavy lines mean α- as well as β-configuration, and R is the following radicals: 
 R=Me, Et, Pr, iso-Pr, Bu, sec-Bu, iso-Bu, tert-Bu.  
 
     
     
         7 . A method for strengthening the top note of a perfume composition, the method comprising adding to said perfume composition a top note strengthening effective amount of a cyclic isolongifolenyl ether of the general formula A:  
       
         
           
           
               
               
           
         
       
       where wavy lines mean α- as well as β-configuration, and R is the following radicals: 
 R=Me, Et, Pr, iso-Pr, Bu, sec-Bu, iso-Bu, tert-Bu.  
 
     
     
         8 . A method for rounding off and/or harmonizing the main notes of a fragrance composition, the method comprising adding to said fragrance composition an effective amount of a cyclic isolongifolenyl ether of the general formula A:  
       
         
           
           
               
               
           
         
       
       where wavy lines mean (α- as well as β-configuration, and R is the following radicals: 
 R=Me, Et, Pr, iso-Pr, Bu, sec-Bu, iso-Bu, tert-Bu.  
 
     
     
         9 . A method for conveying or strengthening a musk and/or patchouli aspect in a fragrance composition, the method comprising adding to said fragrance composition an effective amount of a cyclic isolongifolenyl ether of the general formula A:  
       
         
           
           
               
               
           
         
       
       where wavy lines mean α- as well as β-configuration, and R is the following radicals: 
 R=Me, Et, Pr or iso-Pr.