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US4999439A Expired / Lapsed US ⏱️ 0.0 years remaining

Alkyl-substituted tetra- or hexahydrobenzopyran derivatives, organoleptic uses thereof and process for preparing same

Assignee: International Flavors and Fragrances Inc
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Filing: 1990-03-22
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Granted: 1991-03-12
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Expires: 2010-03-22
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Abstract

Abstract Described are alkyl-substituted tetra- or hexahydrobenzopyran derivatives defined according to one of the generic structures: ##STR1## wherein Z is a moiety in the alternative either ##STR2## wherein in the moiety having the structure: ##STR3## R' is methyl or ethyl and in the moiety having the structure: ##STR4## one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds; wherein R 1 and R 2 taken separately represent hydrogen or C 1 -C 3 lower alkyl (with the proviso that R 1 and R 2 are not both hydrogen) or R 1 and R 2 taken together complete a C 5 or C 6 cycloalkyl moiety; and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, hair preparations, cosmetic powders and perfumed polymers. Also described are synthesis processes for preparing such alkyl-substituted tetra- or hexahydrobenzopyran derivatives by means of reacting isopulegol or an isomer thereof with an acetal or ketal.

Inventors

  • 👤 Mark A. Sprecker
  • 👤 Robert P. Belko
  • 👤 Marie R. Hanna
  • 👤 Charles E. J. Beck
  • 👤 Salvatore M. Brucato

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 03:23
CPC Classifications
C; C07; C07D; C07D311/00; C07D311/02; C07D311/94; C07D311/74; C11; C11B; C11B9/00; C11B9/0069; C11B9/0073; C11B9/008; C11D; C11D3/00; C11D3/50

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 110 words
At least one alkyl-substituted tetra- or hexahydrobenzopyran derivative defined according to the structure: ##STR160## wherein Z is a moiety selected from the group consisting of: ##STR161## wherein in the moiety: ##STR162## one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed represent carbon-carbon single bonds; wherein R' is hydrogen methyl or ethyl; wherein R 1 and R 2 taken separately are the same or different hydrogen or C 1 -C 3 alkyl or R 1 and R 2 taken together complete a C 5 or C 6 cycloalkyl moiety with the proviso that R 1 and R 2 are not both hydrogen.
Claim 2
Dependent Claim 110 words
At least one alkyl-substituted tetra- or hexahydrobenzopyran derivative defined according to the structure: ##STR160## wherein Z is a moiety selected from the group consisting of: ##STR161## wherein in the moiety: ##STR162## one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed represent carbon-carbon single bonds; wherein R' is hydrogen methyl or ethyl; wherein R 1 and R 2 taken separately are the same or different hydrogen or C 1 -C 3 alkyl or R 1 and R 2 taken together complete a C 5 or C 6 cycloalkyl moiety with the proviso that R 1 and R 2 are not both hydrogen.
Claim 3
Dependent Claim 49 words
A mixture of alkyl-substituted tetra- or hexahydrobenzopyran derivatives of claim 1 defined according to the structure: ##STR163## wherein in each of the compounds of the mixture one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines is carbon-carbon single bond.
Claim 4
Dependent Claim 15 words
An alkyl-substituted tetra- or hexahydrobenzopyran derivative of claim 1 defined according to the structure: ##STR164##
Claim 5
Dependent Claim 50 words
A mixture of alkyl-substituted tetra- or hexahydrobenzopyran derivatives of claim 1 defined according to the structure: ##STR165## wherein in each of the compounds of the mixture one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines is a carbon-carbon single bond.
Claim 6
Dependent Claim 15 words
An alkyl-substituted tetra- or hexahydrobenzopyran derivative of claim 1 defined according to the structure: ##STR166##
Claim 7
Dependent Claim 49 words
A mixture of alkyl-substituted tetra- or hexahydrobenzopyran derivatives of claim 1 defined according to the structure: ##STR167## wherein in the mixture in each of the compounds one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds.
Claim 8
Dependent Claim 15 words
An alkyl-substituted tetra- or hexahydrobenzopyran derivative of claim 1 defined according to the structure: ##STR168##
Claim 9
Dependent Claim 50 words
A mixture of alkyl-substituted tetra- or hexahydrobenzopyran derivatives of claim 1 defined according to the structure: ##STR169## wherein in the mixture in each of the compounds one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines is a carbon-carbon single bond.
Claim 10
Dependent Claim 15 words
An alkyl-substituted tetra- or hexahydrobenzopyran derivative of claim 1 defined according to the structure: ##STR170##
Claim 11
Dependent Claim 50 words
A mixture of alkyl-substituted tetra- or hexahydrobenzopyran derivatives of claim 1 defined according to the structure: ##STR171## wherein in the mixture in each of the compounds one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines is a carbon-carbon single bond.
Claim 12
Dependent Claim 15 words
An alkyl-substituted tetra- or hexahydrobenzopyran derivatives of claim 1 defined according to the structure: ##STR172##
Claim 13
Dependent Claim 50 words
A mixture of alkyl-substituted tetra- or hexahydrobenzopyran derivatives of claim 1 defined according to the structure: ##STR173## wherein in the mixture in each of the compounds one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines represents a carbon-carbon single bond.
Claim 14
Dependent Claim 15 words
An alkyl-substituted tetra- or hexahydrobenzopyran derivative of claim 1 defined according to the structure: ##STR174##
Claim 15
Dependent Claim 200 words
An alkyl substituted tetra- or hexahydrobenzopyran derivative-containing composition of matter, said alkyl substituted tetra- or hexahydrobenzopyran derivative being defined according to the structure: ##STR175## produced according to the process comprising the step of reacting a ketal or acetal having the structure: ##STR176## with isopulegol having the structure: ##STR177## in the presence of a catalytic amount of protonic acid catalyst at a temperature of between 75° C. and 100° C. with the mole ratio of acetal or ketal:isopulegol varying from 2 moles acetal or ketal:1 mole isopulegol to 1 mole acetal or ketal:1 mole isopulegol according to the reaction: ##STR178## wherein Z is a moiety selected from the group consisting of: ##STR179## wherein in the moiety having the structure: ##STR180## one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines is a carbon-carbon single bond; wherein R' is methyl or ethyl; and wherein R 1 and R 2 taken separately are the same or different hydrogen or C 1 -C 3 alkyl or R 1 and R 2 taken together complete a C 5 or C 6 cycloalkyl moiety with the provisio that R 1 and R 2 are not both hydrogen.
Claim 16
Dependent Claim 200 words
An alkyl substituted tetra- or hexahydrobenzopyran derivative-containing composition of matter, said alkyl substituted tetra- or hexahydrobenzopyran derivative being defined according to the structure: ##STR175## produced according to the process comprising the step of reacting a ketal or acetal having the structure: ##STR176## with isopulegol having the structure: ##STR177## in the presence of a catalytic amount of protonic acid catalyst at a temperature of between 75° C. and 100° C. with the mole ratio of acetal or ketal:isopulegol varying from 2 moles acetal or ketal:1 mole isopulegol to 1 mole acetal or ketal:1 mole isopulegol according to the reaction: ##STR178## wherein Z is a moiety selected from the group consisting of: ##STR179## wherein in the moiety having the structure: ##STR180## one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines is a carbon-carbon single bond; wherein R' is methyl or ethyl; and wherein R 1 and R 2 taken separately are the same or different hydrogen or C 1 -C 3 alkyl or R 1 and R 2 taken together complete a C 5 or C 6 cycloalkyl moiety with the provisio that R 1 and R 2 are not both hydrogen.
Claim 17
Dependent Claim 120 words
A mixture of compounds having the structures: ##STR181## wherein R 1 is C 1 -C 3 lower alkyl and wherein in the mixture of compounds having the structure: ##STR182## in each of the compounds one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines is a carbon-carbon single bond produced according to the process comprising the step of reacting isopulegol having the structure: ##STR183## with an aldehyde having the structure: ##STR184## in the presence of a catalytic amount of protonic acid catalyst at a temperature of between 75° and 100° C. at with a mole ratio of aldehyde:isopulegol being from 2 moles aldehyde:1 mole isopulegol to 1 mole aldehyde:1 mole isopulegol.
Claim 18
Dependent Claim 120 words
A mixture of compounds having the structures: ##STR181## wherein R 1 is C 1 -C 3 lower alkyl and wherein in the mixture of compounds having the structure: ##STR182## in each of the compounds one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines is a carbon-carbon single bond produced according to the process comprising the step of reacting isopulegol having the structure: ##STR183## with an aldehyde having the structure: ##STR184## in the presence of a catalytic amount of protonic acid catalyst at a temperature of between 75° and 100° C. at with a mole ratio of aldehyde:isopulegol being from 2 moles aldehyde:1 mole isopulegol to 1 mole aldehyde:1 mole isopulegol.

References Cited (Backward Citations)

SU534454A1 Cited
SU638597A1 Cited
SU618374A1 Cited
SU620487A1 Cited
JPS5528970A Cited
US4233226A Cited
US4217371A Cited
US4268445A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1994-03-11 1994-09-10 1995-03-12 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1998-03-11 1998-09-10 1999-03-12 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2002-03-11 2002-09-10 2003-03-12 $7700.00 Window Closed / Lapsed

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