Route to α- tocopheryl alkanoates and percursors thereof

US7622591B2 · kind B2 · utility

Assignee

• DSM IP ASSETS B.V. · NL

Inventors

• Werner Bonrath · Kaiseraugst, CH
• Manfred Breuninger · Glückstadt, DE
• Grégory Malaisé · Saint-Louis, FR
• Thomas Netscher · Bad Krozingen, DE

Key dates

• Filing date: Sep 2, 2004
• Grant date: Nov 24, 2009
• Expiry date: Oct 9, 2025

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D311/72
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

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.