Use of isomerically pure or highly isomer-enriched cis- or trans-(2-isobutyl-4-methyl-tetrahydropyran-4-yl)acetate

Patent metadata

Field	Value
Publication number	US-10160931-B2
Application number	US-201515514101-A
Country	US
Kind code	B2
Filing date	Sep 25, 2015
Priority date	Sep 26, 2014
Publication date	Dec 25, 2018
Grant date	Dec 25, 2018

Abstract

The present invention relates to the use of isomerically pure or highly isomerically enriched cis- or trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate for use as aroma chemicals. The invention further relates to a process for the preparation of isomerically pure or highly isomerically enriched cis- or trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate and the products obtainable by this process. The invention further relates to a fragrance or aroma substance composition which comprises isomerically pure or highly isomerically enriched cis- or trans-(2-isobutyl-4-methyltetra-hydropyran-4-yl) acetate, a method for imparting, and/or boosting an odor or taste of a product, and also perfumed or aromatized products which comprise isomerically pure or highly isomerically enriched cis- or trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate.

First claim

The invention claimed is:

1. A process for the preparation of isomerically pure cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate of the formula (I.1) or of isomerically pure trans -(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate of the formula (I.2) or of an isomer mixture of (I.1) and (I.2), where the weight fraction of (I.1) or the weight fraction of (I.2) in the isomer mixture, based on the total weight of (I.1) and (I.2), is in a range from 90% by weight to less than 100% by weight,
comprising:
i) reacting an isomer mixture of cis-2-(2-methylpropyl)-4-hydroxy-4-methyltetrahydropyran (II.1) and trans-2-(2-methylpropyl)-4-hydroxy-4-methyltetrahydropyran (II.2)

with a compound of the formula CH 3 C(═O)-X, in which X is Cl, Br or CH 3 C(═O)O,
ii) optionally subjecting the reaction mixture obtained in step i) to a separation to give at least one fraction which comprises isomerically pure (I.1) or isomerically pure (I.2) or an isomer mixture of (I.1) and (I.2), where the weight fraction of (I.1) or the weight fraction of (I.2) in the isomer mixture, based on the total weight of (I.1) and (1.2), is in a range from 90% by weight to less than 100% by weight.

2. An isomerically pure cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate of the formula (I.1) or an isomer mixture of cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.1) and trans-(2-isobutyl-4methyltetrahydropyran-4-yl) acetate (I.2), in which the weight fraction of cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.1), based on the total weight of cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.1) and trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.2) is in a range from 90% by weight to less than 100% by weight.

3. An isomerically pure trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate of the formula (I.2) or an isomer mixture of cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.1) and trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.2), in which the weight fraction of trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.2), based on the total weight of cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.1) and trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.2), is in a range from 90% by weight to less than 100% by weight.

4. A fragrance or aroma substance composition, comprising
a) isomerically pure cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate of the formula (I.1) or isomerically pure trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate of the formula (I.2) or an isomer mixture of cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.1) and trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.2), where the weight fraction of cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.1), based on the total weight of cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.1) and trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.2) is in a range from 90% by weight to less than 100% by weight, or the weight fraction of trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.2), based on the total weight of cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.1) and trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.2) is in a range from 90% by weight to less than 100% by weight,
b) optionally at least one further aroma chemical different from the compounds (I.1) and (I.2), and
c) optionally at least one diluent,

with the proviso that the composition comprises at least one component b) or c).

5. The composition according to claim 4 , comprising the component a) in a weight fraction of from 1 to 50% by weight, based on the total weight of the composition.

6. The composition according to claim 4 , comprising the component a) in a weight fraction of from 0.1 to 70% by weight, based on the total weight of the composition.

7. A method for imparting and/or intensifying an odor or taste of a product with an iris-like note, a bergamot-like note, a linalyl acetate-like note, a woody note or a pepper/nutmeg-like note, comprising bringing the product into contact with an organoleptically effective amount of an isomerically pure cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate of the formula (I.1) or an isomer mixture, where the weight fraction of cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I. 1), based on the total weight of cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.1) and trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (L2), is in a range from 90% by weight to less than 100% by weight.

8. A method for imparting and/or intensifying an odor or taste of a product with a jasmine-like note, a leather-like note or a strong fruit-like note, in which the product is brought into contact with an organoleptically effective amount of an isomerically pure trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate of the formula (I.2) or an isomer mixture, where the weight fraction of trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.2), based on the total weight of cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.1) and trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.2) is in a range from 90% by weight to less than 100% by weight.

9. A perfumed or aromatized product, comprising an organoleptically effective amount of isomerically pure cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate of the formula (I.1) or of isormerically pure trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate of the formula (I.2) or of an isomer mixture of cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.1) and trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.2), comprising an organoleptically effective amount of a fragrance or aroma substance composition as defined in claim 4 .

10. The product according to claim 9 , selected from the group consisting of scent dispensers and fragrances perfumes, detergents and cleaners, cosmetic compositions, bodycare compositions, hygiene articles, products for oral and dental hygiene, scent dispensers, fragrances, pharmaceutical compositions and crop protection compositions.

11. The use of isomerically pure cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate of the formula (I.1) or of an isomer mixture, where the weight fraction of cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.1), based on the total weight of cis-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.1) and trans-(2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.2), is in a range from 90% by weight to less than 100% by weight, for the partial or complete replacement of linalyl acetate in a fragrance or aroma substance composition comprising linalyl acetate or in a product aromatized or perfumed with linalyl acetate.

Assignees

• Basf Se

Inventors

• Stork Timon
• Rüdenauer Stefan
• Klos Margarethe
• Pelzer Ralf
• Krause Wolfgang

Classifications

• C11B9/008 Primary

  the hetero rings containing six atoms · CPC title

• A23L27/2052

  having oxygen or sulfur as the only hetero atoms · CPC title

• C07D309/10

  Oxygen atoms · CPC title