CHAPTER IV - Tertiary Alcohols (I:R = OH)

Abstract

This chapter discusses eight methods for the synthesis of basic tertiary alcohols. Most hydrochlorides of the basic tertiary alcohols are stable in neutral aqueous solution but are readily dehydrated in acid solution. The hydroxyl group in branched alcohols having a methyl group in α-position is sterically hindered. Such alcohols require drastic treatment for dehydration; thionyl chloride may be used for this purpose. The bases of the amino alcohols are crystalline solids. They form crystalline hydrochlorides and methiodides. They can be distilled only at extremely low pressures. In the unbranched alcohols derived from open dialkylamines, the lengthening of the alkyl-groups results in a progressive decrease of the melting points. The side chain branching has irregular influence on the melting points. Quaternization with methyl halides increases the potency of the bases, while alkyl halides with more than two carbon atoms produce progressively less and less active quaternary salts. The basic tertiary alcohols are chemically and pharmacologically closely related to the trihexyphenidyl group of parasympatholytic and nicotinolytic compounds.