26281-43-6Relevant articles and documents
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Armstrong
, (1872)
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Sulfonation of chloro- and dichloroanisoles with concentrated aqueous sulfuric acid and sulfur trioxide. Demethylation of chloroanisolesulfonic acids in sulfuric acid systems
Wit, Peter de,Cerfontain, Hans
, p. 418 - 425 (2007/10/02)
The nine chloro- and dichloroanisoles have been sulfonated with sulfuric acid.The observed sulfonic acid isomer distributions are determined mainly by the ortho- and para-directing effect of the methoxy substituent.In the reaction with sulfuric acid, the initially formed chloro- and dichloroanisolesulfonic acids are demethylated to give the corresponding phenolsulfonic acids.Demethylation occurs only in those cases where the methoxy substituent is sterically hindered by an o-chloro and/or o-sulfo substituent.Reaction of 2,3- and 3,5-dichloroanisole with fuming sulfuric acid yields initially the 4,6- and 2,4-disulfonic acids, respectively.The disulfonic acids are converted to the corresponding hydrogen sulfates either by direct sulfodemethylation or by protodemethylation followed by subsequent sulfation.The 2,3-dichloro-4,6-disulfophenyl hydrogen sulfate cyclizes to the 1,3,2,4-benzodioxadithiin 2,2,4,4-tetraoxide 4.The sulfonation of the chloro- and dichloroanisoles with SO3 in the solvents nitromethane or CCl3F leads only to sulfodeprotonation.
Communications from the Laboratory of the London Institution. On the action of potassic sulphite on the haloid derivatives of phenol
Armstrong, Henry E.,Harrow, George
, p. 474 - 477 (2007/11/12)
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