1-(7,10,10-trimethyl-4-bicyclo(6.2.0)decanyl)ethanone as novel aroma chemical

Patent metadata

Field	Value
Publication number	US-9950982-B2
Application number	US-201515536452-A
Country	US
Kind code	B2
Filing date	Dec 18, 2015
Priority date	Dec 19, 2014
Publication date	Apr 24, 2018
Grant date	Apr 24, 2018

Abstract

The present invention relates to 1-(7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl)ethanone, the use of 1-(7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl)ethanone as a fragrance or as flavor, to a method for imparting or modifying a scent or a flavor to a composition by including said compound into such composition, to a fragrance containing composition and/or a fragrance material containing said compound and to a process for preparing 1-(7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl)ethanone.

First claim

The invention claimed is:

1. 1-(7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl)ethanone.

2. 1-(7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl)ethanone as claimed in claim 1 in the form of 1-[(1R,4R/S,7R/S,8S)-7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl]ethanone.

3. 1-[(1R,4R/S,7R/S,8S)-7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl]ethanone as claimed in claim 2 in the form of a mixture of stereoisomers thereof, which predominantly contains the (4R,7R)- and (4R,7S)-isomer.

4. 1-[(1R,4R/S,7R/S,8S)-7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl]ethanone as claimed in claim 2 in the form of a mixture of stereoisomers thereof, which predominantly contains the (4S,7R)- and (4S,7S)-isomer.

5. 1-[(1R,4R/S,7R/S,8S)-7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl]ethanone as claimed in claim 2 in the form of a mixture of stereoisomers thereof, which predominantly contains the (4R,7R)-isomer, the (4R,7S)-isomer, the (4S,7R)-isomer or the (4S,7S)-isomer.

6. 1-(7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl)ethanone as claimed in claim 1 having a purity of at least 80%.

7. A fragrance or flavor comprising the 1-(7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl)ethanone according to claim 1 .

8. The fragrance or flavor of claim 7 , where 1-(7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl)ethanone is present in the form of a mixture of stereoisomers thereof, which predominantly contains the (4S,7R)- and (4S,7S)-isomer.

9. The fragrance or flavor of claim 7 , wherein the fragrance or flavor is a composition which further comprises a carrier.

10. The fragrance or flavor of claim 9 , where the composition is selected from the group consisting of laundry detergents, fabric detergents, cosmetic preparations, fragranced hygiene articles, foods, food supplements, fragrance dispensers, perfumes, pharmaceutical preparations and crop protection compositions.

11. A method of imparting or modifying a scent or a flavor to a composition, which method comprises incorporating the 1-(7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl)ethanone according to claim 1 into a composition in such an amount that imparts or modifies the scent or flavor of the composition.

12. A fragrance containing composition and/or a fragrance material, which comprises the 1-(7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl)ethanone according to claim 1 and a carrier material.

13. A process for preparing 1-(7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl)ethanone, which comprises
i) providing 1-(10,10-dimethyl-7-methylene-4-bicyclo[6.2.0]decanyl)ethanone,
ii) hydrogenating 1-(10,10-dimethyl-7-methylene-4-bicyclo[6.2.0]decanyl)ethanone with hydrogen in the presence of a hydrogenation catalyst.

14. The process of claim 13 , where the composition containing 1-(10,10-dimethyl-7-methylene-4-bicyclo[6.2.0]decanyl)ethanone provided in step i) is obtained by reacting 4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene with N 2 O.

15. The process of claim 14 , where (4R,4E,9S)-4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene is reacted with N 2 O to obtain 1-[(1R,4R/S,8S)-10,10-dimethyl-7-methylene-4-bicyclo[6.2.0]decanyl]ethanone.

16. The process of claim 13 , where step i) or both steps i) and ii) are performed in a continuous manner.

17. The process of claim 13 , further comprising the purification of the reaction mixture obtained in step ii) by distillation.

Assignees

• Basf Se
• Basf Se Reitstoetter Kinzebach & Partner

Inventors

• Bru Roig Miriam
• Rüdenauer Stefan
• Pelzer Ralf

Classifications

• C07C2602/26

  the ring system containing ten carbon atoms · CPC title

• C11B9/00

  Essential oils; Perfumes · CPC title

• C07C49/323 Primary

  having keto groups bound to condensed ring systems · CPC title

• C07B2200/07

  Optical isomers · CPC title

• C07C49/307 Primary

  to a seven- to twelve-membered ring · CPC title