Process for the preparation of 1-(2,6,6-trimethylcyclohexyl)-alkan-3-ols

Patent metadata

Field	Value
Publication number	US-9920007-B2
Application number	US-201515526962-A
Country	US
Kind code	B2
Filing date	Nov 17, 2015
Priority date	Nov 18, 2014
Publication date	Mar 20, 2018
Grant date	Mar 20, 2018

Abstract

The present invention relates to a process for the preparation of 1-(2,6,6-trimethylcyclohexylyalkan-3-ols, in particular 1-(2,6,6-trimethylcyclohexyl)-hexan-3-ol. The invention further relates to 5-alkoxy-1-(2,6,6-trimethylcyclohexenyl)-1-alken-3-ones and the use of these as a fragrance or as flavor, to a fragrance containing composition and/or a fragranced product containing 5-alkoxy-1-(2,6,6-trimethylcyclohexenyl)-1-alken-3-ones and to a method for imparting or modifying a scent or a flavor to a composition by including said alkoxyalkenones into such composition.

First claim

The invention claimed is:

1. A process for preparing a compound of formula (I),

where R 1 is selected from C 1 -C 4 -alkyl, the process comprising:
i) reacting a composition containing α-ionone, β-ionone or γ-ionone or mixtures thereof with an aldehyde R 1 —(C═O)H in the presence of a base and an alcohol R 2 —OH to yield a reaction product mixture comprising at least one compound of formula (I.a),

where
R 2 is C 1 -C 6 -alkyl, and
the broken lines represent a single double bond that can be arranged in one of the three positions drawn,

ii) treating the reaction product obtained in step i) with an acid to yield a ketone of formula (I.b)

and
iii) hydrogenating the ketone I.b with hydrogen in the presence of a hydrogenation catalyst.

2. The process of claim 1 , where the base used in step i) is selected from metal hydroxides.

3. The process of claim 1 , where R 1 is methyl.

4. The process of claim 1 , where the alcohol R 2 —OH is selected from methanol, ethanol or isopropanol.

5. The process of claim 1 , where the reacting step i) is performed at a temperature in a range of from −10 to 50° C.

6. The process of claim 1 , where the reaction product mixture of the step i) is directly applied in step ii).

7. The process of claim 1 , where the hydrogenation catalyst comprises at least one metal selected from the grout consisting of nickel, rhodium and palladium.

8. The process of claim 1 , further comprising distilling a reaction mixture obtained in the step iii).

9. The process of claim 1 , where the steps i) and ii) or the step iii), or all steps i) to iii), are performed in a continuous manner.

10. A compound of formula (I.a),

where
R 1 is C 1 -C 4 -alkyl,
R 2 is C 1 -C 6 -alkyl and
the broken lines represent a single double bond that can be arranged in one of the three positions drawn.

11. The compound according to claim 10 , where R 1 is methyl and R 2 is C 1 -C 3 -alkyl.

12. The compound 5-methoxy-1-(2,6,6-trimethylhexen-1-yl)hex-1-en-3-one.

13. A fragrance or a flavor composition comprising
a) at least one compound (I.a), as defined in claim 10 ,
b) optionally at least one aroma chemical different from the compounds (I.a), and
c) optionally at least one carrier,
with the proviso that the composition comprises at least one of the components b) or c).

14. A product comprising at least one compound (I.a), as defined in in claim 10 , the product 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.

15. A method of imparting or modifying a scent or a flavor to a composition, which method comprises incorporating at least one compound of the formula (I.a), as defined in claim 10 , into a composition in such an amount that imparts or modifies the scent or flavor of the composition.

Assignees

• Basf Se

Inventors

• Rüdenauer Stefan
• Pelzer Ralf
• Bru Roig Miriam
• Swaminathan Vijay Narayanan
• Hindalekar Shrirang
• Gupte Nitin
• Kolambkar Prachin

Classifications

• A23L27/203

  Alicyclic compounds · CPC title

• C07C29/175 Primary

  with simultaneous reduction of an oxo group · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title

• C07C403/16 Primary

  not being part of —CHO groups · CPC title

• C11B9/0034

  the ring containing six carbon atoms · CPC title