International Flavors & Fragrances Inc.

William I Taylor

Braja D Mookherjee

Frederick L Schmitt

John B Hall

Takao Yoshida

Venkatesh Kamath

Richard A Wilson

James M Sanders

Ira D Hill

John J Kryschuk

Paul Martin Koppel

Described are perfume and fragrance compositions and perfumed articles including soaps, detergents, powders as well as colognes containing 2,2,3-trimethyl-3-cyclopenten-1-ylalkyl, alkenyl and alkylidene, cyclohexanois, having the generic structure: ##STR1## wherein at least one of the lines ++++ is a carbon-carbon single bond and the other of the lines ++++ is either a carbon-carbon single bond or a carbon-carbon double bond, which imparts thereto woody, sandalwood aromas.

2,2,3-Trimethyl-3-cyclopenten-1-ylalkyl, alkenyl and alkylidene,

Described are perfume and fragrance compositions and perfumed articles including soaps, detergents, powders as well as colognes containing 2,2,3-trimethyl-3-cyclopenten-1-ylalkenyl and alkylidene secondary alkanols, alkanones, cycloalkanols and cycloalkanones having the generic structure: ##STR1## wherein one of the lines +++++ is a carbon-carbon double bond and the other of the lines +++++ is a carbon-carbon single bond; wherein X is carbinol having the structure: ##STR2## or carbonyl having the structure ##STR3## wherein A' is hydrogen, CH.sub.3, C.sub.2 H.sub.5 or --CH.sub.2 --; wherein B' is hydrogen, CH.sub.3, C.sub.2 H.sub.5 or --CH.sub.2 --; where n is 0, 1 or 2; wherein each of the dashed lines are the same and each represents a carbon-carbon single bond or no bond; wherein A' and B' are both --CH.sub.2 -- when n is 1 or 2 and the dashed line is a carbon-carbon single bond or A' is hydrogen and B' is C.sub.2 H.sub.5 or CH.sub.3 or both A' and B' are each CH.sub.3 or A' is C.sub.2 H.sub.5 and B' is CH.sub.3 when n is 0 and the dashed line represents no bond, which imparts thereto rich, musky, cedar woody, sandalwood, sweet, floral, ionone-like, soft-fruity (apricot), green and earthy aromas with resinous topnotes and nutty oily nuances. Also described is a process for preparing such compounds according to the reaction schemes: ##STR4## wherein the lines +++++ A', B', the dashed lines and n are as defined above wherein M is alkaline metal.

2,2,3-Trimethyl-3-cyclopenten-1-ylalkenyl and alkylidene secondary

Described are perfume compositions and processes for producing same which compositions comprise in an aroma augmenting or enhancing quantity at least one compound having the structure: ##STR1## wherein m is 0 or 1; wherein one of the lines + + + + is a carbon-carbon single bond and the other of the lines + + + + is a carbon-carbon double bond and wherein X is carbinol having the structure: ##STR2## and at least one adjuvant selected from the group consisting of natural perfume oils, synthetic perfume oils, alcohols, aldehydes, ketones other than those defined herein, esters, nitriles and lactones. Also described are colognes containing compounds having the above structure and ethanol and water.

Described are perfume and fragrance compositions and perfumed articles including soaps, detergents, powders as well as colognes containing 2,2,3-trimethyl-3-cyclopenten-1-ylalkenyl and alkylidene secondary alkanols, alkanones, cycloalkanols and cycloalkanones having the generic structure: ##STR1## wherein one of the lines + + + + + is a carbon-carbon double bond and the other of the lines + + + + + is a carbon-carbon single bond; wherein X is carbinol having the structure: ##STR2## or carbonyl having the structure ##STR3## wherein A' is hydrogen, CH.sub.3, C.sub.2 H.sub.5 or --CH.sub.2 --; wherein B' is hydrogen,CH.sub.3, C.sub.2 H.sub.5 or --CH.sub.2 --; where n is 0, 1 or 2; wherein each of the dashed lines are the same and each represents a carbon-carbon single bond or no bond; wherein A' and B' are both --CH.sub.2 -- when n is 1 or 2 and the dashed line is a carbon-carbon single bond or A' is hydrogen and B' is C.sub.2 H.sub.5 or CH.sub.3 or both A' and B' are each CH.sub.3 or A' is C.sub.2 H.sub.5 and B' is CH.sub.3 when n is 0 and the dashed line represents no bond, which imparts thereto rich, musky, cedar woody, sandalwood, sweet, floral, ionone-like, soft-fruity (apricot), green and earthy aromas with resinous topnotes and nutty oily nuances. Also described is a process for preparing such compounds according to the reaction schemes: ##STR4## wherein the lines + + + + + A', B', the dashed lines and n are as defined above wherein M is alkaline metal.

Described is a process for augmenting or enhancing the aroma of a solid or liquid anionic, cationic or nonionic detergent comprising the step of adding to a solid or liquid anionic, nonionic or cationic detergent base an aroma augmenting or enhancing quantity of at least one 2,2,3-trimethyl-3-cyclopenten-1-ylalkenyl and alkylidene cycloalkanol or cycloalkanone defined according to the structure: ##STR1## wherein m is 0 or 1; wherein one of the lines ++++ is a carbon-carbon single bond and the other of the lines ++++ is a carbon-carbon double bond and wherein X is selected from the group consisting of carbonyl having the structure: ##STR2## and carbinol having the structure: ##STR3##

Use of 2,2,3,-trimethyl-3-cyclopenten-1-ylalkenyl and alkylidene

Described are perfume and fragrance compositions and colognes containing 2,2,3-trimethyl-3-cyclopenten-1-ylalkenyl and alkylidene secondary alkanols, alkanones, cycloalkanols and cycloalkanones having the generic structure: ##STR1## wherein one of the lines +++++ is a carbon-carbon double bond and the other of the lines +++++ is a carbon-carbon single bond; wherein X is carbonyl having the structure ##STR2## wherein A' is hydrogen, CH.sub.3, C.sub.2 H.sub.5 or --CH.sub.2 --; wherein B' is hydrogen, CH.sub.3, C.sub.2 H.sub.5 or --CH.sub.2 --; where n is 0, 1 or 2; wherein each of the dashed lines are the same and each represents a carbon-carbon single bond or no bond; wherein A' and B' are both --CH.sub.2 -- when n is 1 or 2 and the dashed line is a carbon-carbon single bond or A' is hydrogen and B' is C.sub.2 H.sub.5 or CH.sub.3 or both A' and B' are each CH.sub.3 or A' is C.sub.2 H.sub.5 and B' is CH.sub.3 when n is 0 and the dashed line represents no bond, which imparts thereto rich, musky, cedar woody, sandalwood, sweet, floral, ionone-like, soft-fruity (apricot), green and earthy aromas with resinous topnotes and nutty oily nuances.

2,2,3-Trimethyl-3-cyclopenten-1-yl-alkenyl and alkylidene cycloalkanones

2,2,3-Trimethyl-3-cyclopenten-1-ylalkenyl- and alkylidene-cycloalkanones

Described is a process for preparing an equilibrium mixture containing 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1,3-butanedione and its enol, which equilibrium mixture contains compounds having the structures: ##STR1## which process involves first reacting a methyl magnesium halide with 1-acetyl-2,6,6-trimethyl-1,3-cyclohexadiene to form a first organometallic compound; reacting the first organometallic compound with an acetyl halide to form a second organometallic compound, a novel intermediate; and then reacting said second organometallic compound with a hydrolyzing agent such as aqueous acid to form said equilibrium mixture.

Process for preparing

A process is described for reacting 'myrac aldehyde' having the structure: ##STR1## (which structure is representative of a mixture of two compounds, one where the carboxaldehyde is in the '4' position and the other wherein the carboxaldehyde is in the '5' position) with an acid hydrating agent at a temperature of from 0.degree. up to 120.degree. C, to produce a mixture containing a major proportion of 4-(4'-methyl-4'-hydroxyamyl)-.DELTA..sup.3 -cyclohexene carboxaldehyde and a minor proportion of 3-(4'-methyl-4'-hydroxyamyl)-.DELTA..sup.3 -cyclohexene carboxaldehyde (otherwise termed 'Lyral') having the structure: ##STR2## and a minor proportion of 3-(4'-methyl-4'-hydroxyamyl)-.DELTA..sup.3 -cyclohexene carboxaldehyde having the structure: ##STR3## which mixture possesses a sweet, lilac-lily aromatic odor and isolating a mixture of the two carboxaldehydes. The products produced by the aforementioned process are useful in various aspects of perfumery.

Process for producing mixture containing

A process for effecting at least the partial resolution of a first pinene mixture containing alpha pinene and beta pinene is described comprising the sequential steps of (i) admixing diethylene glycol with said first pinene mixture of alpha pinene and beta pinene thus forming a second pinene mixture; (ii) subjecting the resulting second pinene mixture of alpha pinene, beta pinene and diethylene glycol to fractional azeotropic distillation yielding (A) a distillate which is a two liquid phase non-emulsified composition the first phase of which is the lower phase and which consists essentially of diethylene glycol and the second phase of which is the upper phase and which consists essentially of a third pinene mixture consisting essentially of alpha pinene and beta pinene, substantially richer in alpha pinene than said first pinene mixture and (B) a bottoms mixture, which is a two liquid phase, non-emulsified composition, the first phase of which is the lower phase and which consists essentially of diethylene glycol and the second phase of which is the upper phase and which consists essentially of alpha-pinene and beta-pinene substantially richer in beta-pinene than said first pinene mixture; and (iii) physically separating said first phase from said second phase by means of decantation. A preferred manner of carrying out such process comprises the sequential steps of (i) first removing, in the absence of azeotroping agent, by means of distillation a portion of the .alpha.-pinene from the first pinene mixture whereby 80% of the .alpha.-pinene is removed from the first pinene mixture of .alpha.-pinene and beta pinene and whereby said first pinene mixture is enriched in concentration of beta pinene, thereby forming a second pinene mixture; (ii) admixing diethylene glycol with the resulting second pinene mixture of alpha pinene and beta pinene to form a third pinene mixture; (iii) subjecting the resulting third pinene mixture of alpha pinene, beta pinene and diethylene glycol to fractional azeotropic distillation yielding (A) a distillate which is a two liquid phase non-emulsified composition; the first phase of which is a lower phase and which consists essentially of diethylene glycol and the second phase of which is the upper phase and which consists essentially of a fourth pinene mixture consisting essentially of alpha pinene and beta pinene substantially richer in alpha pinene than said second pinene mixture and (B) a bottoms mixture, which is a two liquid phase, non-emulsified composition, the first phase of which is the lower phase and which consists essentially of diethylene glycol and the second phase of which is the upper phase and which consists essentially of alpha-pinene and beta-pinene substantially richer in beta-pinene than said first pinene mixture; and (iv) physically separating said first phase from said second phase by decantation.

Growing community of inventors

Summit, NJ, United States of America

William I Taylor