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solvent inert to CaC2?

Started by El_Zorro, January 03, 2003, 09:53:00 AM

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El_Zorro

What solvents are inert towards CaC2?  More specifically, one that acetamide would be fairly soluble in.


pHarmacist

What does this has to do with: Novel synthetic routes to psychoactive materials


El_Zorro

Well, I didn't really mention it in the question but I was asking this so that I could start forming a procedure for dehydrating acetamide to acetonitrile.  So if anybody has thoughts on that too, I'd like to hear them.


Rhodium

You want a solvent not containing any acidic hydrogens or other functional groups sensitive to bases. Such solvents include hydrocarbons (like hexane/toluene) and ethers (THF/Et2O).

Chlorinated hydrocarbons (DCM, chloroform) might react, so don't use them just to be safe. Esters, alcohols and ketones and any solvents not properly dried are directly unsuitable.

Tengo

Would CaC2 dissolve in benzaldehyde, forming (after acidification) 1,4-diphenyl-1,4-dihydroxy-2-butyne?
CaC2 + 2Ph-CHO -> Ph-C(OH)-C---C-C(OH)-Ph

Rhodium


Tengo

Just a thought... C22- being such a strong base, that it would add to the carbonyl and making a hydroxy... SN2 basically... Well... a nucleophile attack anyway...
If CaC2 won't dissolve in benzaldehyde, then this wouldn't work. But perhaps with another solvent...?

Tengo

Anybody...any knowledge about this...?

PolytheneSam

Maybe you could heat acetamide and CaC2 together without a solvent.  Try a small amount in a test tube.  You could connect a one hole rubber stopper and 90 degree piece of glass tubing to the test tube and then connect a condenser to it and see if you can distill off any CH3CN.