US4493790A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Organoleptic use of isopropyl tetramethylindanes
Assignee: International Flavors and Fragrances Inc
•
Filing: 1983-10-12
•
Granted: 1985-01-15
•
Expires: 2003-10-12
Abstract
Abstract Described are isopropyl tetramethylindan musks defined according to the generic structure: ##STR1## wherein R 3 and R 4 are each acetyl or methyl with the provisos: (a) one of R 3 or R 4 is methyl; (b) when R 4 is methyl, then R 3 is acetyl and (c) when R 4 is acetyl, R 3 is methyl and organoleptic uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles.
Inventors
- 👤 Mark A. Sprecker
- 👤 Robert P. Belko
- 👤 Roger E. Greene
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 21:37
CPC Classifications
C; C11; C11B; C11B9/00; C11B9/0042; C11B9/0046; C11B9/0049; C07; C07C; C07C45/00; C07C45/45; C07C45/46; C07C49/00; C07C49/76; C07C49/782; C07C49/792; C07C5/00; C07C5/22; C07C5/27; C07C5/29
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
338 words
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 perfume composition, cologne or perfumed article an aroma augmenting or enhancing quantity of a product consisting essentially of a mixture of compounds having the structures: ##STR70## wherein a major proportion of the mixture consists of the compound having the structures: ##STR71## produced according to the process consisting of the steps of: (i) first rearranging hexamethyl tetralin with an aluminum chloride catalyst according to the reactions: ##STR72## said first reaction taking place in the presence of tetrachloro ethylene solvent which is saturated with aluminum trichloride, said reaction taking place in the presence of an excessive aluminum chloride, the weight ratio of aluminum chloride:tetrachloro ethylene varying from about 35:100 up to about 60:100, the temperature of said first reaction varying from about -10° C. up to +10° C. and the time of reaction varying from about 0.5 hours up to about 10 hours, the weight ratio of tetrachloro ethylene:hydrocarbon reactant having the structure: ##STR73## wherein one of R 1 or R 2 is hydrogen and the other of R 1 or R 2 is methyl varying from about 100:75 down to about 100:25; and (ii) acylating the resulting product with a compound having the structure: ##STR74## wherein Z represents a moiety selected from the group consisting of acetoxy, chloro and bromo, the reaction being carried out at a temperature of from about -10° up to about +20° C.; the mole ratio of compound having the structure: ##STR75## to the compound defined according to the structure: ##STR76## wherein one of R 1 or R 2 is hydrogen and the other of R 1 or R 2 is methyl varying from about 0.5:1 up to 1:0.5; and then (iii) subjecting the resulting reaction product to fractional distillation whereby a mixture of compounds having the structures: ##STR77## is isolated with the major part of said mixture being compounds having the structures: ##STR78##
Claim 2
Dependent Claim
338 words
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 perfume composition, cologne or perfumed article an aroma augmenting or enhancing quantity of a product consisting essentially of a mixture of compounds having the structures: ##STR70## wherein a major proportion of the mixture consists of the compound having the structures: ##STR71## produced according to the process consisting of the steps of: (i) first rearranging hexamethyl tetralin with an aluminum chloride catalyst according to the reactions: ##STR72## said first reaction taking place in the presence of tetrachloro ethylene solvent which is saturated with aluminum trichloride, said reaction taking place in the presence of an excessive aluminum chloride, the weight ratio of aluminum chloride:tetrachloro ethylene varying from about 35:100 up to about 60:100, the temperature of said first reaction varying from about -10° C. up to +10° C. and the time of reaction varying from about 0.5 hours up to about 10 hours, the weight ratio of tetrachloro ethylene:hydrocarbon reactant having the structure: ##STR73## wherein one of R 1 or R 2 is hydrogen and the other of R 1 or R 2 is methyl varying from about 100:75 down to about 100:25; and (ii) acylating the resulting product with a compound having the structure: ##STR74## wherein Z represents a moiety selected from the group consisting of acetoxy, chloro and bromo, the reaction being carried out at a temperature of from about -10° up to about +20° C.; the mole ratio of compound having the structure: ##STR75## to the compound defined according to the structure: ##STR76## wherein one of R 1 or R 2 is hydrogen and the other of R 1 or R 2 is methyl varying from about 0.5:1 up to 1:0.5; and then (iii) subjecting the resulting reaction product to fractional distillation whereby a mixture of compounds having the structures: ##STR77## is isolated with the major part of said mixture being compounds having the structures: ##STR78##
Claim 3
Dependent Claim
91 words
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 perfume composition, cologne or a perfumed article an aroma augmenting or enhancing quantity of a composition of matter consisting essentially of a mixture of compounds having the structures: ##STR79## with a major proportion of the mixture being compounds having the structures: ##STR80## produced according to the process of the steps of: (i) intimately admixing the compound having the structure: ##STR81##
Claim 4
Dependent Claim
91 words
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 perfume composition, cologne or a perfumed article an aroma augmenting or enhancing quantity of a composition of matter consisting essentially of a mixture of compounds having the structures: ##STR79## with a major proportion of the mixture being compounds having the structures: ##STR80## produced according to the process of the steps of: (i) intimately admixing the compound having the structure: ##STR81##
Claim 5
Dependent Claim
185 words
with the compound having the structure: ##STR82## wherein one of R 1 or R 2 is hydrogen and the other of R 1 or R 2 is methyl; and wherein Z is a moiety selected from the group consisting of acetoxy, chloro and bromo, the reaction being carried out in the presence of tetrachloro ethylene saturated with aluminum chloride and in the presence of an excess of aluminum chloride with the weight ratio of aluminum trichloride:tetrachloro ethylene varying from about 1:4 up to about 1:1; the weight ratio of aluminum chloride:hydrocarbon defined according to the structure: ##STR83## varying from about 0.5:1 up to about 1:0.5; the reaction temperature varying from about -10° C. up to about +10° C.; the reaction time varying from about 3 hours up to about 10 hours; the mole ratio of compound having the structure: ##STR84## to compound having the structure: ##STR85## varying from about 0.5:1 up to about 1:0.5; and then (ii) fractionally distilling the resulting product thereby recovering a mixture of compounds having the structures: ##STR86## with a major proportion of the mixture being compounds having the structures: ##STR87##
Claim 6
Dependent Claim
185 words
with the compound having the structure: ##STR82## wherein one of R 1 or R 2 is hydrogen and the other of R 1 or R 2 is methyl; and wherein Z is a moiety selected from the group consisting of acetoxy, chloro and bromo, the reaction being carried out in the presence of tetrachloro ethylene saturated with aluminum chloride and in the presence of an excess of aluminum chloride with the weight ratio of aluminum trichloride:tetrachloro ethylene varying from about 1:4 up to about 1:1; the weight ratio of aluminum chloride:hydrocarbon defined according to the structure: ##STR83## varying from about 0.5:1 up to about 1:0.5; the reaction temperature varying from about -10° C. up to about +10° C.; the reaction time varying from about 3 hours up to about 10 hours; the mole ratio of compound having the structure: ##STR84## to compound having the structure: ##STR85## varying from about 0.5:1 up to about 1:0.5; and then (ii) fractionally distilling the resulting product thereby recovering a mixture of compounds having the structures: ##STR86## with a major proportion of the mixture being compounds having the structures: ##STR87##
References Cited (Backward Citations)
US3509215A
Cited
US4352748A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-01-15 | 1988-07-16 | 1989-01-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-01-15 | 1992-07-16 | 1993-01-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-01-15 | 1996-07-16 | 1997-01-15 | $7700.00 | Window Closed / Lapsed |