Process for the preparation of 4-methylpent-3-en-1-ol derivatives

Patent metadata

Field	Value
Publication number	US-9381507-B2
Application number	US-201414763162-A
Country	US
Kind code	B2
Filing date	Jan 21, 2014
Priority date	Jan 23, 2013
Publication date	Jul 5, 2016
Grant date	Jul 5, 2016

Abstract

The present invention concerns a process for the preparation with high selectivity of a compound of formula (I) by isomerization at room temperature of compound of formula (II) in the presence of a complex of formula [Ru(dienyl) 2 H]X.

First claim

What is claimed is:

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

wherein X represents a CHO, CH(OR 1 ) 2 , COOH, COOR 2 , CON(R 3 ) 2 or a CH 2 OH group, R 1 representing when taken separately a C 1-4 alkyl or when taken together a C 2-8 alkanediyl group, R 2 representing a C 1-5 alkyl group, R 3 representing when taken separately a C 1-4 alkyl or when taken together a C 3-8 alkanediyl group optionally comprising an ether functional group; and
R represents a C 1-12 alkyl or C 5-12 cycloalkyl group, a C 2-12 alkenyl or C 5-12 cycloalkenyl group, or a C 6-12 alkandienyl or C 6-12 cycloalkandienyl group;
by the isomerization of the corresponding compound of the formula (II)

wherein R and X have the same meaning as in formula (I);
said isomerization being performed in the presence of a complex of formula:
[Ru(dienyl) 2 H]A  (III)

wherein
dienyl represents a C 5 -C 22 hydrocarbon group comprising a carbon-carbon double bond and a moiety C═C—C − ; and
A is a weakly or non-coordinating anion.

2. A process according to claim 1 , characterized in that said R is a group of formula

wherein m is 0, 1 or 2.

3. A process according to claim 1 , characterized in that said X represents a CH 2 OH group.

4. A process according to claim 1 , characterized in that said A represents NO 3 − , HSO 4 − , BF 4 − , PF 6 − , SbF 6 − , AsF 6 − , F − or R x SO 3 − wherein R x is a fluoride atom or a C 1-8 alkyl or C 1-10 aromatic group optionally substituted by one to three C 1-4 alkyl groups or C 1-8 fluoroalkylgroup.

5. A process according to claim 1 , characterized in that said A represents NO 3 − , BF 4 − , PF 6 − , SbF 6 − , AsF 6 − , F − or R x SO 3 − wherein R x is a fluoride atom or a C 1-8 alkyl or C 1-8 fluoroalkylgroup.

6. A process according to claim 1 , characterized in that said dienyl is cyclooctadienyl, or norbornadienyl, or 2,4-dimethyl-pentadienyl, or 2,7-dimethyl-octadienyl or cycloheptadienyl or 2,3,4-trimethypenta-1,3-dienyl.

Assignees

• Firmenich & Cie

Inventors

• Riedhauser Jean-Jacques
• Knopff Oliver
• Marinoni Luigi

Classifications

• C07C29/56 Primary

  by isomerisation · CPC title

• B01J31/28

  of the platinum group metals, iron group metals or copper · CPC title

• B01J2531/821

  Ruthenium · CPC title

• B01J31/2291

  Olefins · CPC title

• C07C45/67

  by isomerisation; by change of size of the carbon skeleton · CPC title