Organic compounds

Patent metadata

Field	Value
Publication number	US-9708570-B2
Application number	US-201414900272-A
Country	US
Kind code	B2
Filing date	Jun 27, 2014
Priority date	Jun 28, 2013
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

Abstract

meta-Substituted 3-phenylpropanal derivatives useful in providing watery-marine, floral-aldehydic notes.

First claim

The invention claimed is:

1. A compound of the formula (I)

wherein
R 1 and R 2 are independently selected from hydrogen and methyl with the proviso that at least either R 1 or R 2 is methyl;
R 3 is selected from prop-2-yl, propen-2-yl and cyclopropyl; and
n is 1 or 2.

2. The compound according to claim 1 selected from 3-(3-(4-methylpentyl)phenyl)butanal, 3-(3-isopentylphenyl)-2-methylpropanal, 2-methyl-3-(3-(3-methylbut-3-en-1-yl)phenyl)-propanal, 3-(3-isopentylphenyl)butanal, 3-(3-(2-cyclopropyl ethyl)phenyl)-2-methylpropanal, 3-(3-(2-cyclopropylethyl)phenyl)butanal, and 2-methyl-3-(3-(3-methylbut-3-en-1-yl)phenyl)butanal.

3. The compound according to claim 1 wherein R 2 is methyl.

4. The compound according to claim 1 enriched in the (5) enantiomer.

5. A method comprising utilizing as a fragrance the compound of formula (I)

wherein
R 1 and R 2 are independently selected from hydrogen and methyl with the proviso that at least either R 1 or R 2 is methyl;
R 3 is selected from prop-2-yl, propen-2-yl and cyclopropyl; and
n is 1 or 2.

6. A method for improving, enhancing or modifying a consumer product base by means of the addition thereto a compound of formula (I), or a mixture thereof

wherein
R 1 and R 2 are independently selected from hydrogen and methyl with the proviso that at least either R 1 or R 2 is methyl;
R 3 is selected from prop-2-yl, propen-2-yl and cyclopropyl; and
n is 1 or 2.

7. A fragrance composition comprising
a. at least one compound of formula (I)

wherein
R 1 and R 2 are independently selected from hydrogen and methyl with the proviso that at least either R 1 or R 2 is methyl;
R 3 is selected from prop-2-yl, propen-2-yl and cyclopropyl; and
n is 1 or 2;

b. and at least one other odorant.

8. A fragranced article comprising
a. at least one compound of formula (I)

wherein
R 1 and R 2 are independently selected from hydrogen and methyl with the proviso that at least either R 1 or R 2 is methyl;
R 3 is selected from prop-2-yl, propen-2-yl and cyclopropyl; and
n is 1 or 2;

b. and a consumer product base.

9. The method according to claim 5 wherein the compound of formula (I) is selected from 3-(3-(4-methylpentyl)phenyl)butanal, 3-(3-isopentylphenyl)-2-methylpropanal, 2-methyl-3-(3-(3-methylbut-3-en-1-yl)phenyl)-propanal, 3-(3-isopentylphenyl)butanal, 3-(3-(2-cyclopropyl ethyl)phenyl)-2-methylpropanal, 3-(3-(2-cyclopropylethyl)phenyl)butanal, and 2-methyl-3-(3-(3-methylbut-3-en-1-yl)phenyl)butanal.

10. The method according to claim 6 wherein the compound of formula (I) is selected from 3-(3-(4-methylpentyl)phenyl)butanal, 3-(3-isopentylphenyl)-2-methylpropanal, 2-methyl-3-(3-(3-methylbut-3-en-1-yl)phenyl)-propanal, 3-(3-isopentylphenyl)butanal, 3-(3-(2-cyclopropylethyl)phenyl)-2-methylpropanal, 3-(3-(2-cyclopropylethyl)phenyl)butanal, and 2-methyl-3-(3-(3-methylbut-3-en-1-yl)phenyl)butanal.

11. The fragrance composition according to claim 7 wherein the compound of formula (I) is selected from 3-(3-(4-methylpentyl)phenyl)butanal, 3-(3-isopentylphenyl)-2-methyl propanal, 2-methyl-3-(3-(3-methylbut-3-en-1-yl)phenyl)-propanal, 3-(3-isopentyl phenyl)butanal, 3-(3-(2-cyclopropylethyl)phenyl)-2-methylpropanal, 3-(3-(2-cyclopropylethyl)phenyl)butanal, and 2-methyl-3-(3-(3-methylbut-3-en-1-yl)phenyl)butanal.

12. The fragranced article according to claim 8 wherein the compound of formula (I) is selected from 3-(3-(4-methylpentyl)phenyl)butanal, 3-(3-isopentylphenyl)-2-methylpropanal, 2-methyl-3-(3-(3-methylbut-3-en-1-yl)phenyl)-propanal, 3-(3-isopentylphenyl) butanal, 3-(3-(2-cyclopropylethyl)phenyl)-2-methylpropanal, 3-(3-(2-cyclopropyl ethyl)phenyl)butanal, and 2-methyl-3-(3-(3-methylbut-3-en-1-yl)phenyl)butanal.

Assignees

• Givaudan Sa

Inventors

• Goeke Andreas
• Kraft Philip
• Zou Yue

Classifications

• C07C47/235

  containing six-membered aromatic rings and other rings · CPC title

• A61Q13/00

  Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00) · CPC title

• C07C2601/02

  with a three-membered ring · CPC title

• C07C47/105

  containing rings · CPC title

• C07C47/228

  containing six-membered aromatic rings, e.g. phenylacetaldehyde · CPC title