Alkoxybenzaldehyde derivatives and precursors thereof

Patent metadata

Field	Value
Publication number	US-12018228-B2
Application number	US-201917289950-A
Country	US
Kind code	B2
Filing date	Oct 30, 2019
Priority date	Oct 31, 2018
Publication date	Jun 25, 2024
Grant date	Jun 25, 2024

Abstract

The present invention refers to alkoxybenzaldehyde derivatives and precursors thereof. The invention further refers to perfume compositions and fragranced article comprising them.

First claim

The invention claimed is:

1. A method of using a compound of formula (I) as a fragrance

wherein R 1 is selected from linear or branched C 3 -, C 4 - and C 5 -alkyl and C 3 -, C 4 - and C 5 -alkenyl, the method comprising (a) mixing the compound of formula (I), or a precursor thereof, with a consumer product base, or (b) mixing a fragrance composition comprising the compound of formula (I), or a precursor thereof, with a consumer product base, (c) or entrapping the compound of formula (I) or a precursor thereof with an entrapment material and then mixing it with the consumer product base.

2. A method of using the compound of formula (I) as a fragrance

comprising the step of generating the compound of formula (I) by spontaneous air oxidation of a compound of formula (II)
wherein

R 1 selected from linear or branched C 3 -, C 4 - and C 5 -alkyl and C 3 -, C 4 - and C 5 -alkenyl;
R 2 is selected from the group consisting of
C 4 -C 14 alkyl; C 4 -C 14 alkyl substituted with one —OH group and/or up to two ether groups;
C 4 -C 14 alkenyl; C 4 -C 14 alkenyl substituted with one —OH group or an ether group;
C 5 -C 6 cycloalkyl; C 5 -C 8 cycloalkyl substituted with 1, 2, or 3 groups selected from C 1 -C 6 alkyl and C 2 -C 4 alkylidene;
C 5 -C 8 cycloalkenyl; C 5 -C 8 cycloalkenyl wherein the cycloalkenyl-ring is substituted with 1, 2, or 3 groups selected from C 1 -C 4 alkyl, C 2 -C 4 alkylidene, and C 3 -C 5 cycloalkyl;
(C 1 -C 3 )alkyl(C 5 -C 6 )cycloalkyl wherein the cycloalkyl-ring is optionally substituted with one group selected from —OH group and ═O group, and/or one or two ether group(s), and/or up to four C 1 -C 5 alkyl groups;
(C 1 -C 4 )alkyl(C 5 -C 6 )cycloalkenyl wherein the cycloalkenyl-ring is optionally substituted with one —OH group, and/or one or two ether group(s), and/or up to four C 1 -C 5 alkyl groups;
(C 2 -C 3 )alkenyl(C 5 -C 6 )cycloalkenyl wherein the cycloalkenyl-ring is optionally substituted with one —OH group, and/or one or two ether group(s), and/or up to four C 1 -C 5 alkyl groups;
(C 1 -C 4 )alkyl(C 6 -C 14 )aryl; (C 1 -C 4 )alkyl(C 6 -C 14 )aryl wherein the aryl-ring is substituted with up to 2 groups selected from C 1 -C 4 alkyl, —O—CH 2 —O—, and
—OR 12 wherein R 12 is independently selected from hydrogen and C 1 -C 4 alkyl;
(C 2 -C 8 )alkenyl(C 6 -C 14 )aryl; (C 2 -C 8 )alkenyl(C 6 -C 14 )aryl wherein the aryl-ring is substituted with up to 2 groups selected from C 1 -C 4 alkyl, —O—CH 2 —O—, and
—OR 13 wherein R 13 is independently selected from hydrogen and C 1 -C 4 alkyl;
bi-, tri, or tetracyclic hydrocarbon ring comprising C 8 -C 12 carbon atoms optionally substituted with up to 6 groups selected from C 1 -C 4 alkyl, —O—CH 2 —O—,
and —OR 14 wherein R 14 is independently selected from hydrogen and C 1 -C 4 alkyl; and
R 3 is selected from hydrogen, C 1 -C 5 alkyl, and C 2 -C 5 alkenyl.

3. A compound of formula (II)

wherein
R 1 selected from linear or branched C 3 -, C 4 - and C 5 -alkyl and C 3 -, C 4 - and C 5 -alkenyl;
R 2 is selected from the group consisting of C 4 -C 14 alkyl; C 4 -C 14 alkyl substituted with one —OH group and/or up to two ether groups;
C 4 -C 14 alkenyl; C 4 -C 14 alkenyl substituted with one —OH group or an ether group;
C 5 -C 6 cycloalkyl; C 5 -C 8 cycloalkyl substituted with 1, 2, or 3 groups selected from C 1 -C 6 alkyl and C 2 -C 4 alkylidene;
C 5 -C 8 cycloalkenyl; C 5 -C 8 cycloalkenyl wherein the cycloalkenyl-ring is substituted with 1, 2, or 3 groups selected from C 1 -C 4 alkyl, C 2 -C 4 alkylidene, and C 3 -C 5 cycloalkyl;
(C 1 -C 3 )alkyl(C 5 -C 6 )cycloalkyl wherein the cycloalkyl-ring is optionally substituted with one group selected from —OH group and ═O group, and/or one or two ether group(s), and/or up to four C 1 -C 5 alkyl groups;
(C 1 -C 4 )alkyl(C 5 -C 6 )cycloalkenyl wherein the cycloalkenyl-ring is optionally substituted with one —OH group, and/or one or two ether group(s), and/or up to four C 1 -C 5 alkyl groups;
(C 2 -C 3 )alkenyl(C 5 -C 6 )cycloalkenyl wherein the cycloalkenyl-ring is optionally substituted with one —OH group, and/or one or two ether group(s), and/or up to four C 1 -C 5 alkyl groups;
(C 1 -C 4 )alkyl(C 6 -C 14 )aryl; (C 1 -C 4 )alkyl(C 6 -C 14 )aryl wherein the aryl-ring is substituted with up to 2 groups selected from C 1 -C 4 alkyl, —O—CH 2 —O—, and —OR 12 wherein R 12 is independently selected from hydrogen and C 1 -C 4 alkyl;
(C 2 -C 8 )alkenyl(C 6 -C 14 )aryl; (C 2 -C 8 )alkenyl(C 6 -C 14 )aryl wherein the aryl-ring is substituted with up to 2 groups selected from C 1 -C 4 alkyl, —O—CH 2 —O—, and —OR 13 wherein R 13 is independently selected from hydrogen and C 1 -C 4 alkyl;
bi-, tri, or tetracyclic hydrocarbon ring comprising C 8 -C 12 carbon atoms optionally substituted with up to 6 groups selected from C 1 -C 4 alkyl, —O—CH 2 —O—, and —OR 14 wherein R 14 is independently selected from hydrogen and C 1 -C 4 alkyl; and
R 3 is selected from hydrogen, C 1 -C 5 alkyl, and C 2 -C 5 alkenyl.

4. The compound according to claim 3 selected from
1-butoxy-3-((1E,4Z)-hepta-1,4-dien-1-yl)benzene;
1-butoxy-3-((1E,7Z)-deca-1,7-dien-1-yl)benzene;
1-(4-(3-butoxyphenyl)but-3-en-1-yl)-4-isobutyl-2-methylbenzene;
1-(4-(3-butoxyphenyl)but-3-en-1-yl)-2-isobutyl-4-methylbenzene;
1-(sec-butoxy)-3-((1E,4Z)-hepta-1,4-dien-1-yl)benzene;
1-((1E,4Z)-hepta-1,4-dien-1-yl)-3-(pentyloxy)benzene;
1-((1E,4Z)-hepta-1,4-dien-1-yl)-3-((2-methylallyl)oxy)benzene;
1-((1E,4Z)-hepta-1,4-dien-1-yl)-3-isopropoxybenzene;
1-butoxy-3-(4-(4-(tert-butyl)phenyl)but-1-en-1-yl)benzene;
1-butoxy-3-(4-(4-(tert-butyl)phenyl)-3-methylbut-1-en-1-yl)benzene;
1-butoxy-3-(4-(3-isopropylphenyl)pent-1-en-1-yl)benzene;
11-(3-butoxyphenyl)-2,6-dimethylundeca-6,10-dien-2-ol;
1-butoxy-3-(3-methyldodec-1-en-1-yl)benzene;
5-(4-(3-butoxyphenyl)-2-methylbut-3-en-1-yl)benzo[d][1,3]dioxole;
1-butoxy-3-(tetradeca-1,3-dien-1-yl)benzene;
1-butoxy-3-(3-phenylprop-1-en-1-yl)benzene;
1-butoxy-3-((5E)-undeca-1,5-dien-1-yl)benzene;
5-(5-(3-butoxyphenyl)pent-4-en-1-ylidene)octahydro-1H-4,7-methanoindene;
1-butoxy-3-(4-(4-ethylphenyl)-3,3-dimethylbut-1-en-1-yl)benzene;
1-butoxy-3-(7-methoxy-3,7-dimethylnon-1-en-1-yl)benzene; and
1-butoxy-3-(4-(4-isobutylphenyl)but-1-en-1-yl)benzene.

5. A method of fragrancing a consumer product, comprising adding to a consumer product base a compound of formula (I) as defined in claim 1 , or precursor thereof.

6. The method according to claim 5 , wherein the precursor of the compound of formula (I) is a compound of formula (II) as defined in claim 3 .

7. The method according to claim 5 , wherein the compound of formula (I) is generated by spontaneous air oxidation of a compound of formula (II) as defined in claim 3 when exposed to oxygen.

8. A consumer product comprising a compound of formula (I) as defined in claim 1 , or a precursor thereof and a consumer product base.

9. The consumer product according to claim 8 wherein the consumer product is selected from home care products, perso

Assignees

• Givaudan Sa

Inventors

• Cocito Armanino Nicolas
• Baumgartner Corinne
• Flachsmann Felix

Classifications

• C11D3/50

  Perfumes · CPC title

• C11D3/2072

  Aldehydes-ketones · CPC title

• C11D3/2068

  Ethers · CPC title

• C07D257/04

  Five-membered rings · CPC title

• C07D295/185

  from aliphatic carboxylic acids · CPC title