Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Synthetic Studies of α-Tocopherol. I. Synthesis of α-Tocopheryl Acetate
Takehiko IchikawaTetsuya Kato
Author information
JOURNALS FREE ACCESS

1968 Volume 41 Issue 5 Pages 1224-1228

Details
Abstract

Geraniol (III) was reacted with trimethylhydroquinone (II) in the presence of boron trifluoride in benzene. The product was then acetylated to give a mixture of 2,5,7,8-tetramethyl-2-(4-methyl-3-penten-1-yl)-6-acetyloxychromane (VI) and 2,5,7,8-tetramethyl-2,3-(4,4-dimethylbutano)-6-acetyloxychromane (Vb). The VI was ozonized and decomposed with zinc and acetic acid to give 2,5,7,8-tetramethyl-2-(2-formylethyl)-6-acetyloxychromane (VII). Pseudoionone (VIII) was reduced with sodium borohydride to give pseudoionol (IX), but in certain cases the dehydration of IX occurred during the distillation. VII was condensed with IX by a Wittig reaction to give 2,5,7,8-tetramethyl-2-(4,8,12-trimethyl-3,5,7,11-tridecatetraen-l-yl)-6-acetyloxychromane (X), which was then hydrogenated to give α-tocopheryl acetate (I).

Information related to the author

This article cannot obtain the latest cited-by information.

© The Chemical Society of Japan
Previous article Next article
feedback
Top