US 7,622,591 B2 · Route to α- tocopheryl alkanoates and percursors thereof

Abstract

The present invention is concerned with a novel process for the manufacture of 4alkanoyloxy-2,3,5-trimethylphenyl (E/Z)-phytyl ethers, precursors of α-tocopheryl alkanoates, by cross-metathesis reaction of alkenyl ethers of 1-alkanoyloxy-2,3,6-trimethylhydroquinone with 2,6,10,14-tetramethylpentadecene or a phytol derivative, e.g. an ester, an ether or a silyl ether, in the presence of a cross-metathesis catalyst. As the crossmetathesis catalyst especially ruthenium metal carbene complexes are suitable which possess (a) ruthenium metal center(s), have an electron count of 16 or 18 and are penta- or hexa-coordinated. A further object of the invention is a process for the manufacture of αtocopheryl alkanoates comprising this reaction.

Claims23

Dependent claims

A process for the manufacture of compounds represented by the following formula III

wherein R3 is C2-5-alkanoyloxy,
by the reaction of
a) a compound represented by the following formula I
wherein R′ and R2 are independently from each other H or C1-5-alkyl, with the proviso that at least one of R1 and R2 is not H, and
wherein R3 is as defined above, with
b) a compound represented by the following formula II
wherein R4 is H or CH2—R5,
wherein R5 is formyloxy, C2-5-alkanoyloxy, benzoyloxy, C1-5-alkoxy or OSiR6R7R8,
wherein R6, R7 and R8 are independently from each other C1-6-alkyl or phenyl,
in the presence of a cross-metathesis catalyst, wherein the cross-metathesis catalyst is
wherein Cy is cyclohexyl.

8 more elements

Dependencies are inferred from the claim text.

Facts

Application

10/571,261Filed 2 Sep 2004

Priority

EP 0302087515 Sep 2003

Published

US 2007/0032667 A18 Feb 2007

Granted

24 Nov 2009

Term ends

Not estimatedThe source records don’t support an estimate.

Classification10 codes

C07C 69/017
Esters of carboxylic acids; Esters of carbonic or haloformic acids: esters of hydroxy compounds having the esterified hydroxy group bound to a…
C07C 67/08
Preparation of carboxylic acid esters: by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
C07C 67/28
Preparation of carboxylic acid esters: by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
C07C 67/29
By modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group: by introduction of…

Route to α- tocopheryl alkanoates and percursors thereof

Life of this patent

Route to α- tocopheryl alkanoates and percursors thereof

Life of this patent

Abstract

Claims23