Dsm IP Assets B.v.

Roche Vitamins Inc.

August Ruettimann

Bruno Burdet

Thomas Netscher

Ulla Letinois

Johann Riegl

The present invention relates to a novel synthetic pathway for alpha-tocopherol. The invention discloses different reactions yielding some new intermediates in a very high yield and stereoselectivity.

Synthesis of intermediates for the preparation of alpha-tocopherol

A process for manufacturing a hydroxylated isoflavone of the formula (I) given in the description comprises re-acting an appropriately substituted 2-hydroxydeoxybenzoin of the formula (II), also given in the description, with a formic acid anhydride of the formula HCOOCOR3, wherein Rsignifies C-alkyl or various other groups as given in the description, in presence of a base or in a solvent which acts as a base, and if necessary promoting the ensuing hydrolysis of the so-produced acylated form of the hydroxylated isoflavone of the formula I by acidification. Of particular interest as products of this process are the 5,7dihydroxyisoflavones, e.g. genistein (5,7,4'-trihydroxyisoflavone). Isoflavones display many useful biochemical effects.

Manufacture of isoflavones

A process for the production of 3-hydroxypropionitrile is provided. This process includes (a) reacting acrylonitrile with water at a defined molar ratio in the presence of a weak base under specific temperature and pressure conditions until a conversion in the range of about 40% to about 80% has been achieved; (b) after cooling the mixture obtained in (a), separating off its aqueous phase; (c) distilling off the acrylonitrile from the organic phase remaining after (b); (d) subjecting the mixture obtained in (c) to pyrolysis at specific temperature and pressure conditions in the presence of a basic catalyst to obtain a mixture consisting mainly of 3-hydroxypropionitrile and acrylonitrile; and (e) isolating the desired 3-hydroxypropionitrile by fractional distillation from the mixture obtained in (d). Such a process in which the basic aqueous phase and the acrylonitrile that has been distilled off are recycled represents a preferred embodiment.

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Arlesheim, Switzerland

August Ruettimann