Chapter 17 - Dihydric and polyhydric aralkanols and their oxidation products with functional groups in separate side chains

Abstract

This chapter reviews several side-chain halogenated alkylbenzenes. There are several methods for the preparation of di- and tri-substituted halomethyl benzenes. The reaction of thionyl bromide with 1,2-, 1,3-, 1,4- benzene dicarboxaldehydes yields the corresponding dibromo compounds (BrCH 2 ) 2 C 6 H 4 . Treatment of 1,3-(HOCH 2 ) 2 C 6 H 4 with an aqueous solution of HCl at 130°C under pressure affords 1,3-(CICH 2 ) 2 C 6 H 4 in excellent yield. 1,2-, 1,3- and 1,4-bis(trichlorosilylmethyl) benzenes and related compounds with methyl ring substituents are obtainable from the reaction of bis(chloromethyl)benzenes with trichlorosilane and isopropylamine. 1,2-, 1,3- and 1,4-(BrCH 2 ) 2 C 6 H 4 can be directly converted in high yields into methyl and iso-propyl phthalates yields using silver(II) oxide in methanol or isopropanol respectively. The chapter also reviews di-and poly-hydric aralkanols, thiols and amines. 1,2-Bis(hydroxymethyl)benzene can be prepared conveniently and in good yield by the reduction of phthalic acid with NaBH 4 and I 2 , with Zn(BH 4 ) 2 in 1,2-dimethoxyethane in the presence of trifluoroacetic acid or with Sml 2 by the addition of a base in the presence of a protic solvent at room temperature.