Alkyl enol ether properfume

Patent metadata

Field	Value
Publication number	US-12291691-B2
Application number	US-201917273556-A
Country	US
Kind code	B2
Filing date	Dec 19, 2019
Priority date	Dec 20, 2018
Publication date	May 6, 2025
Grant date	May 6, 2025

Abstract

Described herein are compounds of formula (I) as properfume compounds. In particular, described herein is a method to release a compound being a ketone of formula (II), a formate ester of formula (III), and/or an alcohol of formula (IV) by exposing the compound of formula (I) to an environment wherein it is oxidized. Moreover, a perfuming composition and a perfumed consumer product including at least one compound of formula (I) are also described.

First claim

The invention claimed is:

1. A method to release from a precursor compound, compounds selected from the group consisting of:
a) a ketone of formula

wherein R 1 represents a C 1-15 alkyl, C 2-15 alkenyl, C 3-15 cycloalkyl, C 5-15 cycloalkenyl or C 6-10 aryl group, each optionally substituted with one or more of a C 1-15 alkyl, C 1-15 alkoxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, hydroxy, carboxylic acid and/or C 1-4 carboxylic ester group;
R 2 represents a C 1-15 alkyl group;
R 1 and R 2 , when taken together, form a C 5-15 cycloalkyl, C 5-15 cycloalkenyl, C 4-14 heterocycloalkyl or C 4-14 heterocycloalkenyl group, each optionally substituted with one or more of a C 1-15 alkyl, C 2-15 alkenyl, C 1-15 alkoxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, carboxylic acid, 4-methylcyclohex-3-en-1-yl and/or C 1-4 carboxylic ester group, the heteroatom represents one or more of an oxygen;
R 4 , each independently, represent a hydrogen or a C 1-5 alkyl group; and
R 1 and R 4 , when taken together, form a C 3-15 cycloalkyl or C 5-15 cycloalkenyl group, each optionally substituted with one or more of a C 1-15 alkyl, C 1-15 alkoxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, carboxylic acid and/or C 1-4 carboxylic ester group;
b) a formate ester of formula

wherein R 3 represents a hydrogen, a C 1-15 alkyl, C 2-15 alkenyl, C 3-15 cycloalkyl or C 5-15 cycloalkenyl group, each optionally substituted with one or more a C 1-15 alkyl, C 1-15 alkoxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, carboxylic acid and/or C 1-4 carboxylic ester group; and
R 4 has the same meaning as defined above; and
R 3 and R 4 , when taken together, form a C 3-15 cycloalkyl or C 5-15 cycloalkenyl group, each optionally substituted with one or more of a C 1-15 alkyl, C 1-15 alkoxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, carboxylic acid and/or C 1-4 carboxylic ester group; and
c) an alcohol of formula

wherein R 3 and R 4 have the same meaning as defined above;
wherein the precursor compound comprises a compound of formula (I)

wherein R 1 , R 2 , R 3 and R 4 have the same meaning as defined above;
by exposing the precursor compound of formula (I) to an environment wherein the compound is oxidized.

2. The method according to claim 1 , wherein R 1 represents a C 1-10 alkyl group optionally substituted with a C 6 aryl, C 5-7 cycloalkyl and/or C 5-7 cycloalkenyl group, each optionally substituted with one or more of a C 1-4 alkyl and/or C 1-4 alkoxy group.

3. The method according to claim 1 , wherein R 2 represents a C 1-3 alkyl group.

4. The method according to claim 1 , wherein R 3 represents a C 1-10 alkyl, C 3-10 alkenyl or C 5-15 cycloalkyl group, each optionally substituted with one or more of a C 1-4 alkyl, C 6 aryl and/or C 6 aryloxy group.

5. The method according to claim 1 , wherein at least two of the compounds of formula (II), (III) or (IV) are perfuming ingredients.

6. The method according to claim 1 , wherein the environment wherein the compound is oxidized is air.

7. The method according to claim 1 , wherein the method provides a long-lasting odor to the environment.

Assignees

• Firmenich & Cie

Inventors

• Womack Gary Bernard
• Indradas Brinda

Classifications

• C11D3/50

  Perfumes · CPC title

• C11D3/2068

  Ethers · CPC title

• C07C67/39

  by oxidation of groups which are precursors for the acid moiety of the ester · CPC title

• C07C45/37

  of >C—O—functional groups to >C=O groups · CPC title

• C07C43/215

  having unsaturation outside the six-membered aromatic rings · CPC title