J. Charalambous
1975
Citations
0
Influential Citations
0
Citations
Journal
Journal name not available for this finding
Abstract
Publisher Summary This chapter focuses on side-chain halogenated alkylbenzenes. Several ring substituted 1,4-bis (chloromethyl)benzenes are obtained by direct dichloromethylation of substituted benzenes. Because of the high reactivity of the side-chain halogen atom, both chloro- and bromomethyl-benzenes are used extensively in synthesis. A multitude of reactions leading to cyclic and especially macrocyclic compounds are investigated. The chapter discusses the properties of di- and poly-hydric aralkanols, thiols, and amines. 1,2- 1,3- and 1,4-Bis (hydroxymethyl) benzene can be prepared in high yield from the appropriate bis(chloromethyl)-benzene by reaction with an alkali or alkaline metal acetate followed by hydrolysis. Reduction of phthalic acid with sodium borohydride and boron trifluoride yields 1,2-bis (hydroxymethyl)benzene. This compound can also be obtained by lithiation of benzyl alcohol followed by treatment with formaldehyde. 1,4-Bis (mercaptomethyl) benzene is obtained in 80% yield by the action of sulfurated sodium borohydride on the corresponding chloromethyl compound. This route is an improvement on earlier routes that involved the use of potassium hydrogen sulfide or urea, and give only moderate yields.