Process for the production of 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal

Patent metadata

Field	Value
Publication number	US-11370738-B2
Application number	US-201917046483-A
Country	US
Kind code	B2
Filing date	Apr 8, 2019
Priority date	Apr 11, 2018
Publication date	Jun 28, 2022
Grant date	Jun 28, 2022

Abstract

The present invention relates to an improved way to produce 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal and derivatives thereof.

First claim

The invention claimed is:

1. A process for the production of a compound of formula (I):

the process comprising the steps of:
(i) forming a compound of formula (V):

 wherein
R 1 is H or CH 3 , by the steps comprising:
(ia) forming a Darzens reaction product between
(1) a compound of formula (II):

 wherein
R 1 is as defined previously, and

(2) a compound of formula (III):

 wherein
X is Cl or Br, preferably wherein X is Cl, and
R 2 is C 1 -C 4 -alkyl, wherein

by carrying out the Darzens reaction between the compounds of formulas (II) and (III) at a reaction temperature in a range from −5° C. to 5° C. in the presence of MOR, wherein R is a C 1 -C 4 -alkyl group and M signifies Na + , K + or Cs + , and with from 1.0 to 1.1 mol equivalents of the compound of formula (III), based on the amount of the compound of formula (II), and from 1.0 to 1.1 mol equivalents of MOR, based on the amount of the compound of formula (II), and thereafter

(ib) conducting a saponification reaction of the Darzens reaction product of step (ia) at room temperature (25° C.) in the presence of NaOH to form the compound of formula (V), and then subsequently without heating,

(ii) subjecting the compound of formula (V) to a decarboxylation reaction at room temperature (25° C.) to obtain the compound of formula (I).

2. The process according to claim 1 , wherein step (i) is carried out in at least one solvent.

3. The process according to claim 2 , wherein step (i) is carried out in at least one aliphatic alcohol, in at least one aliphatic hydrocarbon, and/or in at least one aromatic hydrocarbon.

4. The process according to claim 3 , wherein step (i) is carried out in at least one solvent selected from the group consisting of aliphatic C 1 -C 6 alcohols and aliphatic C 5 -C 10 -hydrocarbons.

5. The process according to claim 1 , wherein step (ii) is carried out under normal pressure.

6. The process according to claim 1 , wherein R is methyl or ethyl.

7. The process according to claim 1 , wherein the Darzens reaction product is a compound of formula (IV):

wherein
R1 and R2 are as defined previously.

8. The process according to claim 7 , wherein the step (ia) is practiced without isolating the compound of formula (IV).

9. The process according to claim 8 , wherein step (ii) is practiced without heating the compound of formula (V).

10. The process according to claim 1 , wherein the compound of formula (III) is chloroacetic acid methyl ester and MOR is sodium methylate.

Assignees

• Dsm Ip Assets Bv

Inventors

• Schuetz Jan

Classifications

• C07C45/58 Primary

  in three-membered rings · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title

• C07C47/225

  containing rings other than six-membered aromatic rings · CPC title