Derivatives from 2,5,6-trimethylcyclohex-2-en-1-ol as aroma ingredients
US-2024400497-A1 · Dec 5, 2024 · US
US11958797B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-11958797-B2 |
| Application number | US-202017603177-A |
| Country | US |
| Kind code | B2 |
| Filing date | Apr 3, 2020 |
| Priority date | Apr 15, 2019 |
| Publication date | Apr 16, 2024 |
| Grant date | Apr 16, 2024 |
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The application relates to a process for the preparation of a compound of formula (II) by cyclisation of a polyene of formula (I), and to an intermediate of formula (III). The obtained compounds are useful intermediates in the preparation of specific isoprenoids, preferably in the production of vitamin A and derivatives of vitamin A.
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The invention claimed is: 1. Process for the production of a compound of formula (II) by cyclisation of a compound of formula (I) in the presence of at least one strong Brønsted acid. 2. Process according to claim 1 , wherein the acid is a solid acid. 3. Process according to claim 1 , wherein the acid is an ion-exchange resin, which has sulfonic acid groups. 4. Process according to claim 1 , wherein the acid is a liquid acid. 5. Process according to claim 1 , wherein the acid is a compound of the following formula (VI) R—SO 3 H (VI), wherein R is C 1 -C 4 -alkyl, Cl, CH 3 or CF 3 . 6. Process according to claim 1 , wherein the acid is chosen from the group consisting of CH 3 SO 3 H, ClSO 3 H and CF 3 SO 3 H. 7. Process according to claim 1 , wherein the acid is used in an amount of 0.5 mol-equivalent (in view of the compound of formula (I)) up to 10 mol-equivalent (in view of the compound of formula (I)). 8. Process according to claim 1 , wherein the process is carried out in the presence of at least one inert solvent. 9. Process according to claim 1 , wherein the process is carried out in at least one polar aprotic solvent. 10. Process according to claim 1 , wherein the process is carried out at a temperature of from −50° C. to 50° C. 11. Process according to claim 1 , wherein the process is carried out at a residence time (□) of 5-30 minutes. 12. Process according to claim 1 , wherein the process is carried out batch-wise. 13. Process according to claim 1 , wherein the process is carried out continuously. 14. A compound of formula (III)
containing rings other than six-membered aromatic rings · CPC title
by isomerisation; by change of size of the carbon skeleton · CPC title
the ring being unsaturated · CPC title
having side-chains substituted by doubly-bound oxygen atoms · CPC title
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