High yield aromatic nitration with KNO3/H2SO4 in DCM

[CodeMason]

This is from Rhodium: http://www.rhodium.ws/chemistry/aromatic.nitration.html

Very interesting, as dichloromethane is a common solvent from paint and varnish stores! Near 100% yields too.

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[mongo blongo]

That is very interesting!
The procedure is not very clear though. I don't get this bit-
"A solution of the substrate 1 (5.0 mmol) in CH2Cl2 (8.0 mL) was added dropwise"
Does that mean the KNO3 was filtered out?
And then added dropwise to what?
Is the end product a mixture of HNO3 and CH2Cl2?
The Dichloromethane from paint and varnish stores is a paint and varnish remover and has 5-20% methanol in it as well. (My dad has some)
Would it effect it or could it be removed?


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The goggles do nothing!AAARRRRRHHH!

[CodeMason]

<font face="Verdana, Arial" size="2">The procedure is not very clear though. I don't get this bit-
"A solution of the substrate 1 (5.0 mmol) in CH2Cl2 (8.0 mL) was added dropwise"
Does that mean the KNO3 was filtered out?
And then added dropwise to what?</font>The substrate is the aromatic to be nitrated. It means to dissolve it first in some DCM, then add this dropwise to the original nitrating mixture.
<font face="Verdana, Arial" size="2">Is the end product a mixture of HNO3 and CH2Cl2?</font>The nitrating mixture is of HNO₃, KHSO₄ (salt-acid metathesis) in DCM.
<font face="Verdana, Arial" size="2">... paint store DCM contains 5-20% methanol ...
Would it effect it</font>Not very likely, although some CH₃ONO₂ would form, which is an unstable but powerful explosive. Search forum "methyl nitrate" for more info.
<font face="Verdana, Arial" size="2">could it be removed?</font>Yes, by distillation. My personal choice would be to remove it.

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