Nitration of 1-chloro-2,3-dimethylbenzene in acetic anhydride. Formation and rearomatization of adducts

doi:10.1139/V78-180

Paper

Nitration of 1-chloro-2,3-dimethylbenzene in acetic anhydride. Formation and rearomatization of adducts

Published Apr 15, 1978 · A. Fischer, C. C. Greig

Canadian Journal of Chemistry

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Abstract

Nitration of l-chloro-2,3-dimethylbenzene in acetic anhydride gives the cis and trans isomers of 3-chloro-4,5-dimethyl-4-nitrocyclohexa-2,5-dienyl acetate (29%) and l-chloro-2,3-dimethyl-4-nitro- (46%), -5-nitro- (5%), and -6-nitrobenzene (20%). In formic acid and acidified methanol, exchange of acetate for formate and methoxyl, respectively, occurs and the diastereoisomers of 3-chloro-4,5-dimethyl-4-nitrocyclohexa-2,5-dienyl formate and methyl ether, respectively, are formed. Rearomatization of each isomer of 3-chloro-4,5-dimethyl-4-nitrocyclohexa-2,5-dienyl acetate in acetic acid results in initial isomerization to form the pair of diastereoisomers and subsequent elimination of nitrous acid to form 3-chloro-4,5-dimethylphenyl acetate. In 25% trifluoroacetic acid in deuteriochloroform elimination of acetic acid and migration of the nitro group to form 1-chloro-2,3-dimethyl-4-nitro-benzene and a lesser amount of its 6-nitro isomer is the dominant reaction. In the presence of mesitylene the formation of th...

Study Snapshot

Nitration of 1-chloro-2,3-dimethylbenzene in acetic anhydride leads to the formation of 3-chloro-4,5-dimethyl-4-nitrocyclohexa-2,5-dienyl acetate, which can be rearomatized to form 3-

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Nitration of 1-chloro-2,3-dimethylbenzene in acetic anhydride. Formation and rearomatization of adducts

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