Tert-butyl esters are routinely cleaved by anhydrous acid conditions by loss of the tBu+ cation. TFA in DCM is a common system for this. Neat formic acid, HBr/AcOH and PTSA in refluxing benzene or toluene are also used (see Greene - Protective Groups in Organic Synthesis (2nd ed) p246).
Tert-butyl esters are routinely cleaved by anhydrous acid conditions by loss of the tBu+ cation. TFA in DCM is a common system for this. Neat formic acid, HBr/AcOH and PTSA in refluxing benzene or toluene are also used (see Greene - Protective Groups in Organic Synthesis (2nd ed) p246).
Good to know, the compound I want to nitrate is usually dissolved in a TFA/DCM mixture, so if it can survive that, it can probably survive with the addition of nitric acid.More
If you are happy with the answer please check the accept box. A quick google search for nitration of methyl benzoate produces a good number of hits with lab procedures, including one done in neat sulfuric acid. The only concern would be your workup if you quench into water.More
Tert-butyl esters are routinely cleaved by anhydrous acid conditions by loss of the tBu+ cation. TFA in DCM is a common system for this. Neat formic acid, HBr/AcOH and PTSA in refluxing benzene or toluene are also used (see Greene - Protective Groups in Organic Synthesis (2nd ed) p246).
Methyl esters usually need aq. acid for cleavage.
Tert-butyl esters are routinely cleaved by anhydrous acid conditions by loss of the tBu+ cation. TFA in DCM is a common system for this. Neat formic acid, HBr/AcOH and PTSA in refluxing benzene or toluene are also used (see Greene - Protective Groups in Organic Synthesis (2nd ed) p246).
Methyl esters usually need aq. acid for cleavage.
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