Process of forming 2-(4-isobutyl-2-methylphenyl) propanal

Patent metadata

Field	Value
Publication number	US-10760033-B2
Application number	US-201515516602-A
Country	US
Kind code	B2
Filing date	Nov 12, 2015
Priority date	Nov 12, 2014
Publication date	Sep 1, 2020
Grant date	Sep 1, 2020

Abstract

The regio-selective functionalization of a dialkyl benzene compound

wherein the ratio of the compound functionalized at position (a) to the compound functionalized at the position (b) is at least 70:30, more particularly at least 80:20, still more particularly at least 85:15, and still more particularly at least 90:10, characterised in that the substituent R is an isobutyl group.

First claim

The invention claimed is:

1. A process of regio-selective functionalization of a dialkyl benzene compound according to the following formula

wherein the ratio of the compound functionalized at position (a) to the compound functionalized at the position (b) is at least 70:30, and wherein the substituent R is an isobutyl group,
wherein the process include a carbonylation reaction which introduces a benzaldehyde functionality into the position (a), and
wherein the carbonylation reaction is carried out using HF/BF 3 and carbon monoxide.

2. A process of forming a compound according to the following formula (I)

comprising the step of:
regio-selectively functionalizing a dialkylbenzene compound

wherein the ratio of the compound functionalized at position (a) to the compound functionalized at the position (b) is at least 70:30, and wherein the substituent R is an isobutyl group.

3. A process of forming a compound of the following formula (I)

comprising the steps of: —

and subsequently,
C) the hydrogenation of compound (VI) to provide compound (I).

4. The process of claim 3 , wherein compound (III) is converted to the corresponding dialkylacetal for purification and is then further converted into compound (I).

5. A compound of the following formula IIIb

formed in a process of forming a compound of the following formula (I)

6. The process of claim 4 , wherein the corresponding dialkylacetal is compound IIIb.

7. The process of claim 1 , wherein the wherein the ratio of the compound functionalized at position (a) to the compound functionalized at the position (b) is at least 80:20.

8. The process of claim 7 , wherein the wherein the ratio of the compound functionalized at position (a) to the compound functionalized at the position (b) is at least 85:15.

9. The process of claim 8 , wherein the wherein the ratio of the compound functionalized at position (a) to the compound functionalized at the position (b) is at least 90:10.

10. The process of claim 2 , wherein the wherein the ratio of the compound functionalized at position (a) to the compound functionalized at the position (b) is at least 80:20.

11. The process of claim 10 , wherein the wherein the ratio of the compound functionalized at position (a) to the compound functionalized at the position (b) is at least 85:15.

12. The process of claim 11 , wherein the wherein the ratio of the compound functionalized at position (a) to the compound functionalized at the position (b) is at least 90:10.

13. The process of claim 2 , wherein the step of regio-selectively functionalizing a dialkylbenzene compound is a carbonylation, a chloromethylation, a bromination or a direct conversion into the compound of formula (I).

Assignees

• Givaudan Sa

Inventors

• Chi-Lam Tse
• Lovchik Martin Alan
• Ellwood Simon
• Goeke Andreas

Classifications

• C07C45/74

  combined with dehydration · CPC title

• C11D3/2072

  Aldehydes-ketones · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title

• C07C45/49

  by reaction with carbon monoxide · CPC title

• C11B9/0061 Primary

  compounds containing a six-membered aromatic ring not condensed with another ring · CPC title