A practical approach for regioselective mono-nitration of phenols under mild conditions

This work has studied the effects on the nitration of toluene by 100% nitric(V) acid and a nitric(V) acid/dichloromethane mixture. The results show that the amount of meta-nitrotoluene decreases with decreases in reaction temperature. From 25 °C to –10 °C the amount of metanitrotoluene was less than for nitrating toluene by a nitric(V)acid/dichloromethane mixture than for nitration by 100% nitric(V) acid. Furthermore, from –20 °C to –30 °C results were similar with 2.6% of meta-nitrotoluene in the reaction products. An excess of nitric(V) acid in the nitration of toluene by the nitric(V) acid/dichloromethane mixture than in nitration by 100% nitric(V) acid. Nitration by the nitric(V) acid/dichloromethane mixture is less exothermic and easier to control than nitration by 100% nitric(V) acid.

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A practical approach for regioselective mono-nitration of phenols under mild conditions

Abstract: Cu(NO 3 ) 2 .3H 2 O was demonstrated to be an efficient, regioselective and inexpensive nitrating reagent for the synthesis of mono-nitro substituted phenolic compounds. 12 examples of different phenols were examined. Good yields (67-90%) have been achieved.

Cited by 3 publications

References 29 publications

FeBr2-catalyzed chlorination of aromatic compounds with ButOCl

FeBr2-catalyzed chlorination of aromatic compounds with ButOCl

Yttrium Nitrate mediated Nitration of Phenols at room temperature in Glacial Acetic acid

Badania reakcji nitrowania toluenu za pomocą mieszaniny kwas azotowy(V)/dichlorometan

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