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McHale, David (1959) The preparation and properties of the bz-monomethyltocols. Doctoral thesis, Sir John Cass College.
The earlier attempts to synthesise the Bz-monomethyltocols have been reinvestigated and the isomeric nature of the products determined by paper chromatography. The results have shown that several erroneous conclusions were made by the earlier workers.
Racemic 7-methyltocol (XLIX, page 54) has been synthesised by an unambiguous route and has been shown to have paper chromatographic properties identical with natural η-tocopherol, thereby confirming the structure of the natural compound.
Racemic 8-methyltocol (XVII, page 21) has been synthesised by a new route.
The condensation of phytol with toluquinol 4-methyl ether has been shown to occur more readily in the 5 position (ortho to the methoxyl group) than in the 6 position (ortho to the hydroxyl group). In consequence, the product after demethylation contains a greater proportion of 7-methyltocol than the expected product 8-methyltocol.
Racemic 5-methyltocol (XIX, page 21) has been synthesised by an unambiguous route and differs from natural ε-tocopherol which was previously thought to be 5-methyltocol.
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