892403-71-3

Upstream product

• 2140-82-1 2,6,10,14-tetramethyl-1-pentadecene 
• 848188-73-8 2,3,6-trimethyl-4-[(3-methylbut-2-en-1-yl)oxy]phenyl acetate 
• 76337-16-1 3,7,11,15-tetramethylhexadec-2-en-1-yl acetate 
• 844467-81-8 (E/Z)-(all-rac)-phytyl benzoate 

Relevant academic research and scientific papers

A NEW ROUTE TO α- TOCOPHERYL ALKANOATES AND PERCURSORS THEROF

The present invention is concerned with a novel process for the manufacture of 4alkanoyloxy-2,3,5-trimethylphenyI (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.

MANUFACTURE OF TOCOPHERYL ACETATE

A process for the manufacture of 3-phytyl-2,5,6-trimethylhydroquinone-l-acetate, and optionally therefrom tocopheryl acetate, comprises either C-alkylating 2,3,6-trimethylhydroquinone-l-acetate with isophytol or phytol in the presence of a sulphur(VI) containing catalyst of the formulaR1SO2OH, wherein Rl signifies hydroxy, halogen, lower alkyl, halogenated lower alkyl or aryl, in an aprotic organic solvent, or O-alkylating 2,3,6-trimethylhydroquinone-l-acetate with a phytyl halide in a polar aprotic organic solvent in the presence of a base, and subjecting the so-obtained 4-O-phytyl-2,3,6-trimethylhydroquinone-l-acetate to a rearrangement reaction, and in each case optionally submitting the so-obtained 3-phytyl-2,5,6-trimethylhydroquinone-l-acetate to a ring closure reaction to produce tocopheryl acetate. The invention also includes the novel compound 3-phytyl-2,5,6-trimethylhydroquinone-l-acetate and certain stereoisomers thereof, and also the further novel compound 4-hydroxy-2,3,6-trimethyl-5-[3-(4,8,12-trimethyltridecyl)-but-3enyl]phenyl acetate which itself is one of several isomers of 3-phytyl-2,5,6- trimethylhydroquinone-l-acetate formed by isomerization under the influence of heating, e.g. during its distillation as part of the isolation and purification procedure following its manufacture as indicated above. (All-rac)-α -tocopherol, which may be derived from its acetate, is known to be the most active industrially important member of the vitamin E group.