I am interested in nitrating an aromatic ester in a solution of dichloromethane. I found the following paper that describes creating a nitric acid solution in dichloromethane using KNO3 and sulfuric acid:
Strazzolini P, et al. "Nitric Acid in Dichloromethane Solution. Facile Preparation from Potassium Nitrate and Sulfuric Acid." Tetrahedron Letters 42 (2001) 1387 - 1389.
This paper describes both the nitration of Benzyl Methyl Ester and the nitrolysis of Benzyl Tertbutyl Ester and Phenyl Tertbutyl Ester using their nitric acid in dichloromethane method.
But I am having trouble understanding how they controlled the reactions to get nitration of one ester and nitrolysis of another ester. The reaction conditions seem similar, but the concentration of nitric acid in the nitrolysis reactions is about twice as high as in the nitration reaction. Could the difference be in the tertbutyl group vs the methyl group on the ester?