Abstract
Publisher Summary This chapter focuses on dihydric and polyhydric aralkanols, and their oxidation products. Aryl derivatives of dihydric alcohols; aralkanediols are presented. Phenylethane-1,2-diol, PhCHOHCH2OH, and styrene oxide are now manufactured by oxidation of styrene with peracetic acid. The diol is obtained in good yield when the peracetic acid is diluted 10:1 with water. The chapter also presents aryl derivatives of amino-alcohols; aminoaralkanols. Asymmetric synthesis of 2-amino-1-arylethanols, ArCH(OH)CH2NH2, is achieved by catalytic hydrogenation of amino acetophenones using rhodium complexes. Oxidation of adrenaline with potassium iodate gives 7-iodo-adrenochrome, the structure of which has been confirmed by X-ray analysis. In phenylethanolamines, the onium group influences reactions that usually proceed through aryl-stabilized carbonium ions. Derivatives of 2-alkylamino-1-(4-hydroxyphenyl)-1-ethanol are converted into the β-methylethers in good yield, but etherification of the 4-methoxyphenyl compound cannot be accomplished. Etherification of the free phenol is therefore thought to involve a quinone methide intermediate rather than a carbonium ion. Acid-catalyzed racemization of catecholamines may proceed by a similar mechanism.
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