US3673261A
Expired / Lapsed
US
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Perfume compounds and process for preparing same
Assignee: Procter and Gamble Co
•
Filing: 1969-12-12
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Granted: 1972-06-27
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Expires: 1989-12-12
Abstract
Abstract The compounds 2-methylene-3-exo(trans-4''-methyl-5''-hydroxypent3'' -enyl)bicyclo(2.2.1)heptane, 2-methylene-3-exo-(cis-4''-methyl5''-hydroxypent-3''-enyl)bicyclo(2.2.1)heptane and 2-methylene-3exo(4''-methyl-5''-hydroxypentyl)bicyclo(2.2.1)-heptane, all of which are useful as perfumes, and processes for their preparation are disclosed.
Inventors
- 👤 Herbert C Kretschmar
- 👤 William F Erman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 01:10
CPC Classifications
C; C11; C11B; C11B9/00; C11B9/0042; C11B9/0046; C07; C07C; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/69; C07C47/00; C07C47/20; C07C47/225
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
56 words
admixing in an organic solvent the 2-methyl-3-oxatricyclo(6.2.1.02,7)undec-4-ene obtained in Step (1) with an aqueous mineral acid having a concentration of from 0.001 to 5.0 molar, in a mole ratio of tricyclic compound to acid of from about 1:1 to 1:50 at a temperature of from about 27* to 100* C for from 0.5 to 24 hours;
Claim 2
Dependent Claim
2 words
2-Methylene-3-exo(cis-4''-methyl-5''-hydroxypent-3'' -enyl)bicyclo(2.2.1)heptane.
Claim 3
Dependent Claim
66 words
admixing in an organic solvent the 2-methylene-3-exo(3''-oxopropyl)bicyclo(2.2.1)heptane obtained from Step (1) with (carbethoxyethylidene)triphenyl phosphorane in a molar ratio of bicyclic compound to phosphorane compound of from about 1:1 to 1:5 and a weight ratio of bicyclic compound to solvent of from about 1:2 to 1:50 at a temperature of from about 0* to 50* C for a period of from about 1 to 36 hours; and
Claim 4
Dependent Claim
56 words
admixing in an organic solvent the 2-methyl-3-oxatricyclo(6.2.1.02,7)undec-4-ene obtained in Step (1) with an aqueous mineral acid having a concentration of from 0.001 to 5.0 molar, in a mole ratio of tricyclic compound to acid of from about 1:1 to 1:50 at a temperature of from about 27* to 100* C for from 0.5 to 24 hours;
Claim 5
Dependent Claim
68 words
admixing in an organic solvent the reaction product of Step (2) with (carbethoxyethylidene)triphenyl phosphorane in a molar ratio of said Step (2) reaction product to phosphorane compound of from about 1:1 to 1:5 and a weight ratio of said Step (2) reaction product to solvent of from about 1:2 to 1:50 at a temperature of from about 4* to 100* C for from about 1 to 100 hours.
Claim 6
Dependent Claim
97 words
admixing in an anhydrous organic solvent the reaction product of Step (2) with a reducing agent selected from the group consisting of lithium aluminum hydride, potassium in an alkanol, sodium in an alkanol and lithium in an alkanol in a substantially equivalent molar ratio of said Step (2) reaction product to reducing agent and a weight ratio of said Step (2) reaction product to anhydrous solvent of from about 1:5 to 1:50 under an inert atmosphere at a temperature of from about -50* to 20* C for a period of from about 5 minutes to 2 hours.
Claim 7
Dependent Claim
1 words
2-Methylene-3-exo(4''-methyl-5''-hydroxypentyl)-bicyclo(2.2.1)heptane.
Claim 8
Dependent Claim
68 words
admixing in an organic solvent the reaction product of Step (2) with (carbethoxyethylidene)triphenyl phosphorane in a molar ratio of said Step (2) reaction product to phosphorane compound of from about 1:1 to 1:5 and a weight ratio of said Step (2) reaction product to solvent of from about 1:2 to 1:50 at a temperature of from about 4* to 100* C for from about 1 to 100 hours;
Claim 9
Dependent Claim
78 words
admixing in an anhydrous organic solvent the reaction product of Step (3) with a dehydrating agent in a molar ratio of said Step (3) reaction product to dehydrating agent of from about 100:1 to 1:20 and a weight ratio of said Step (3) reaction product to anhydrous solvent of from about 1:0.5 to 1:50 under inert atmosphere at a temperature of from about -20* to 50* C for a period of from about 0.5 to 3 hours; and
Claim 10
Dependent Claim
12 words
A process for preparing 2-methylene-3-exo(trans-4''-methyl-5''-hydroxypent-3''-enyl)bicyclo(2.2.1) -heptane and 2-methylene-3-exo(cis-4''-methyl-5''-hydroxypent-3''-enyl)bicyclo(2.2.1)heptane comprising the steps of:
Claim 11
Dependent Claim
48 words
admixing in an organic solvent the reaction product obtained in Step (3) with a hydrogenation catalyst under a hydrogen atmosphere at a pressure of from 1 to 10 atmospheres at a temperature of from 27* to 100* C for a period of from about 0.5 to 24 hours;
Claim 12
Dependent Claim
81 words
admixing in an anhydrous organic solvent the reaction product obtained in Step (4) with a dehydrating agent in a molar ratio of said Step (4) reaction product to dehydrating agent of from about 100:1 to 1:20 and a weight ratio of said Step (4) reaction product to anhydrous solvent of from about 1:0.5 to 1: 50 under an inert atmosphere at a temperature of from about -20* to 50* C for a period of from about 0.5 to 3 hours; and
Claim 13
Dependent Claim
97 words
admixing in an anhydrous organic solvent the reaction product of Step (4) with a reducing agent selected from the group consisting of lithium aluminum hydride, potassium in an alkanol, sodium in an alkanol and lithium in an alkanol in a substantially equivalent molar ratio of said Step (4) reaction product to reducing agent and a weight Ratio of said Step (4) reaction product to anhydrous solvent of from about 1:5 to 1:50 under an inert atmosphere at a temperature of from about -50* to 20* C for a period of from about 5 minutes to 2 hours.
Claim 14
Dependent Claim
13 words
A process for preparing 2-methylene-3-exo (trans-4''-methyl-5''-hydroxypent-3''-enyl)bicyclo(2.2.1)heptane and 2-methylene-3-exo(cis-4''-methyl-5''-hydroxypent-3''-enyl) -bicyclo(2.2.1)heptane comprising the steps of:
Claim 15
Dependent Claim
9 words
A Process for preparing 2-methylene-3-exo(4''-methyl-5''-hydroxypentyl)bicyclo(2.2.1)heptane comprising the steps of:
Claim 16
Dependent Claim
100 words
admixing in an anhydrous organic solvent the reaction product obtained in Step (5) with a reducing agent selected from the group consisting of lithium aluminum hydride, potassium in an alkanol, sodium in an alkanol and lithium in an alkanol in a substantially equivalent molar ratio of said Step (5) reaction product to reducing agent and in a weight ratio of said Step (5) reaction product to anhydrous organic solvent of from about 1:5 to 1:50 under an inert atmosphere at a temperature of from about -50* to 20* C for a period of from about 5 minutes to 2 hours.
References Cited (Backward Citations)
US3492330A
Cited
US3478114A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1975-06-27 | 1975-12-27 | 1976-06-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-06-27 | 1979-12-27 | 1980-06-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-06-27 | 1983-12-27 | 1984-06-27 | $7700.00 | Window Closed / Lapsed |