Alkyl-substituted spirodecenone derivatives, organoleptic utility thereof and processes for preparing same

Claim 2

An alkyl-substituted spirodecenone derivative defined according to the structure: ##STR46## wherein one of R 1 or R 2 is methyl and the other of R 1 or R 2 is hydrogen; and wherein R 3 represents C 3 -C 4 alkyl.

Claim 3

A process for augmenting or enhancing the aroma of a consumable material selected from the group consisting of perfume compositions, colognes and perfumed articles comprising the step of adding to said consumable material, an aroma augmenting or enhancing quantity of the product of claim 1.

Claim 4

The product of claim 1 having the structure: ##STR47##

Claim 5

The product of claim 1 having the structure: ##STR48##

Claim 6

The product of claim 1 having the structure: ##STR49##

Claim 7

The product of claim 1 having the structure: ##STR50##

Claim 8

A mixture of alkyl-substituted spirodecenone derivatives having the structures: ##STR51##

Claim 9

A mixture of alkyl-substituted spirodecenone derivatives having the structures: ##STR51##

Claim 10

A mixture of alkyl-substituted spirodecenone derivatives having the structures: ##STR52##

Claim 11

A mixture of alkyl-substituted spirodecenone derivatives having the structures: ##STR52##

Claim 12

A process for augmenting or enhancing the aroma of a consumable material selected from the group consisting of perfume compositions, colognes and perfumed articles comprising the step of adding to said consumable material, an aroma augmenting or enhancing quantity of the product of claim 7.

Claim 13

A process for augmenting or enhancing the aroma of a consumable material selected from the group consisting of perfume compositions, colognes and perfumed articles comprising the step of adding to said consumable material, an aroma augmenting or enhancing quantity of the product of claim 8.

Claim 14

A product containing a mixture of compounds defined according to the structure: ##STR53## wherein one of R 1 or R 2 is hydrogen and the other of R 1 or R 2 is methyl and R 3 is the same C 3 -C 4 alkyl produced according to the process consisting essentially of the steps of: (i) reacting an alkylidenecyclopentanone having the structure: ##STR54## with isoprene having the structure: ##STR55## in the presence of a Lewis acid catalyst and an inert solvent for a period of time sufficient to cause the production of a significant quantity of the compounds having the structure: ##STR56## the reaction temperature varying from about 5° C. up to about 50° C. and the reaction time varying from about 1 hour up to about 15 hours with the mole ratio of alkylidenecyclopentanone to isoprene varying from about 0.5:1.5 up to about 1.5:0.5 and then (ii) recovering the compounds having the structure: ##STR57## from the resulting reaction product by fractional distillation.

Claim 15

A product containing a mixture of compounds defined according to the structure: ##STR53## wherein one of R 1 or R 2 is hydrogen and the other of R 1 or R 2 is methyl and R 3 is the same C 3 -C 4 alkyl produced according to the process consisting essentially of the steps of: (i) reacting an alkylidenecyclopentanone having the structure: ##STR54## with isoprene having the structure: ##STR55## in the presence of a Lewis acid catalyst and an inert solvent for a period of time sufficient to cause the production of a significant quantity of the compounds having the structure: ##STR56## the reaction temperature varying from about 5° C. up to about 50° C. and the reaction time varying from about 1 hour up to about 15 hours with the mole ratio of alkylidenecyclopentanone to isoprene varying from about 0.5:1.5 up to about 1.5:0.5 and then (ii) recovering the compounds having the structure: ##STR57## from the resulting reaction product by fractional distillation.

Claim 16

The product of claim 11 wherein R 3 is isopropyl with said fractional distillation being carried out at a vapor temperature of from 109°-110° C. and a vacuum of 2.5 mm/Hg pressure.

Claim 17

The product of claim 11 wherein R 3 is n-butyl with said fractional distillation being carried out at a vapor temperature of from 110°-118° C. and a vacuum of from 0.8-1.6 mm/Hg pressure.

Claim 18

A process for augmenting or enhancing the aroma of a consumable material selected from the group consisting of perfume compositions, colognes and perfumed articles comprising the step of adding to said consumable material an aroma augmenting or enhancing quantity of the product of claim 12.

Claim 19

A process for augmenting or enhancing the aroma of a consumable material selected from the group consisting of perfume compositions, colognes and perfumed articles comprising the step of adding to said consumable material an aroma augmenting or enhancing quantity of the product of claim 13.