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Chromic
(Synaptic Self-Mutilator) 04-10-03 21:41 No 425454 |
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Preparing NAOT | Bookmark | |||||
A few trials: 1) 7ml o-toluidine, 14ml acetic acid (prep from NaOAc). Reflux 3hrs. Pour into 125ml water. 3g NAOT. 31% yield. 2) 32ml 2-aminotoluene, 64ml acetic acid (prep from NaOAc). Reflux (2-5p). Pour into 575ml water. 18.1g. 41% 3) 27.5ml OT, 55ml glacial AcOH. Reflux. (3-8p). Pour into 500ml water. 15.3g. 35% 4) 50ml OT, 100ml glacial AcOH. Reflux (1-4p). Pour into 900ml water. 24.6g. 35% What the fuck is going wrong here? With Ac2O, everyone speaks of a minimum 80% yield. Would adding some sulfuric acid up the yields, or would it just end up making o-toluidine sulfate instead of catalyzing the condensation to make N-acetyl-orthotoluidine? |
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Antoncho (Official Hive Translator) 04-11-03 06:02 No 425570 |
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MgSO4? | Bookmark | |||||
IIRC, Cheapskate mentioned adding MgSO4 to bind water... i'll try to dig up some data on cryst. temps of some crystallohydrates..... lemmesee.... CaSO4*2H20 : -1,5H2O/128 C; -0,5H2O/163 Ñ (permanently loses its ability to bind water upon total dehydration) CaCl2*6H2O : -4H2O/45 C; -2H2O/>250 Ñ MgBr2*6H2O: mp 172 C (obviously, w/out losing water) MgSO4*7H2O: -6H2O/150 C; -H2O/200 C CuSO4*5H2O: -2H2O/100 C; -2H2O/150 C; -H2O/250 Ñ ZnSO4*7H2O: -7H2O/280 Ñ ZnCl2 also completely loses water at circa 320 C. Would that suffice for your needs, amigo? ![]() Yours, Antoncho |
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moo (Hive Bee) 04-11-03 06:12 No 425574 |
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Complexes ruin the party | Bookmark | |||||
According to ../rhodium /equipme |
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Antoncho (Official Hive Translator) 04-11-03 06:45 No 425577 |
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Yep, you're right, Moo. | Bookmark | |||||
I didn't think of this at 1st, but of course, zinc or aluminium cpds are too acidic for using w/amines, and copper also forms complexes w/both aliphatic and aromatic amines (this rxn can bee used as a test, see, e.g., http://www.chemistry.ccsu.edu/glagovich/ So, we're back to what we started at: good ol' dehydrated Epsom salt ![]() Antoncho |
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Chromic (Synaptic Self-Mutilator) 04-12-03 05:27 No 425942 |
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Hmmm | Bookmark | |||||
Perhaps three hours time wasn't long enough (and that 30 minutes extra you went made the difference) or maybe it was not using ice-cold water... I'm really at a loss. These reagents are supposed to be lab grade. I'll try some dried MgSO4 if this latest run doesn't work, but I fear it's not going to bind the water at the reflux temperature of the mixture. |
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