I commented on a thread someone made over making APAAN using sodium metal and alcohol, and I suggested using powdered sodium alkoxides for convenience.
Now, I'm not trying to fact check them, more check if my thinking is right.
The APAAN synthesis used ethyl acetate, which my understanding has to be very dry, no water. Would using an excess of sodium methoxide, powder or hand made, eliminate the water enough so the reaction could proceed?
Say, one uses a common drying agent like magnesium sulfate, to get the bulk of the water out, and then one uses say 10% excess of sodium alkoxide compared to what is needed in order to react with any present water.
My thinking is based on the chemistry that alkoxides react with water to form sodium hydroxide and the respective alcohol. If I understand correctly, sodium alkoxides are already stronger bases than the respective hydroxide. So that shouldn't hurt things, nor should the alcohol produced, just adding a touch more solvent.
Methoxide would be the ideal alkoxide, as the methanol produced won't draw in atmospheric water as much as it doesn't form an azeotrope. Is this correct thinking?
Could excess alkoxide be used to dry the ethyl acetate, and allow the reaction to proceed? That is all I'm concerned about.
Drying ethyl acetate otherwise requires phosphorous or sieves, and I'd prefer to just throw in more sodium methoxide
Now, I'm not trying to fact check them, more check if my thinking is right.
The APAAN synthesis used ethyl acetate, which my understanding has to be very dry, no water. Would using an excess of sodium methoxide, powder or hand made, eliminate the water enough so the reaction could proceed?
Say, one uses a common drying agent like magnesium sulfate, to get the bulk of the water out, and then one uses say 10% excess of sodium alkoxide compared to what is needed in order to react with any present water.
My thinking is based on the chemistry that alkoxides react with water to form sodium hydroxide and the respective alcohol. If I understand correctly, sodium alkoxides are already stronger bases than the respective hydroxide. So that shouldn't hurt things, nor should the alcohol produced, just adding a touch more solvent.
Methoxide would be the ideal alkoxide, as the methanol produced won't draw in atmospheric water as much as it doesn't form an azeotrope. Is this correct thinking?
Could excess alkoxide be used to dry the ethyl acetate, and allow the reaction to proceed? That is all I'm concerned about.
Drying ethyl acetate otherwise requires phosphorous or sieves, and I'd prefer to just throw in more sodium methoxide