1968 Volume 41 Issue 5 Pages 1224-1228
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).
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