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for DMF in the benzo wacker: real-time question
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| Author | Topic: IPA for DMF in the benzo wacker: real-time question |
| Methyl
Man Member |
posted 10-06-1999 11:30 PM
Hi all, Let's say that hypothetically, right now a guy I don't know is doing a benzo wacker using IPA instead of DMF because he had run out of DMF, and because he wanted to try it after reading another bee post of his success doing it. But he is surprised by the absence of the exothermically-generated warmth (during/after the safrole addition) he had seen with past benzo wackers using DMF. He wonders, in real time right now theoretically (!!), if this is bad because that heat is needed and if he should add some heat to get it to 50C for a while. Can anyone aid him with insight in this fictitious exercise? thanx |
| lucky Member |
posted 10-08-1999 11:27 AM
This cannot be done, is what Rhodium said to me when I asked this question. You need a non-protic polar solvent. DMF is and IPA isn't. The funny thing is I also have read a post by a hive member that did
this, or said it could be done. He also mention that xylene could be used
instead. Just wish I could find the |
| Methyl
Man Member |
posted 10-08-1999 12:08 PM
"Benzo wacker secrets" by Hellman (novel discourse). This is the same post that inspired AGIDK to try this. The guy says it worked, and I doubt he would have posted that if he had not taken it all the way to confirmed ketone (hope not anyway!!) Hellman, if you're reading this, please post here to confirm whether the ketone thus produced (w/IPA) proved to be "aminatable." So far everything looks fairly normal, but on the workup AGIDK noticed that the "tomato soup" color of the aqueous solution was not as dark as it had been with DMF, and that as stated above, the mild exothermic part of the reaction always seen with DMF did not take place. But the extraction into DCM seemed to be the right color. AGIDK intends to finish the workup and distill on Monday, which will be revealing although not final proof. AGIDK decided to add some external heat to try to get the thing up to about 50C where he always saw the standard benzo wacker go on its own. He got it up there, in fact it peaked around 63C, maintained heat on its own for a little while, then drifted back down to ambient temp. He will let you all know how it turns out. |
| hellman Member |
posted 10-10-1999 09:31 PM
Not, me, nor a little tree, said quite circumstancually, ThaT with glee and admirbility the sucess i promise you will see,. Heat as per old skool hellman |
| Methyl
Man Member |
posted 10-11-1999 04:21 PM
Well, just got a call from AGIDK, he says the proof (that IPA will work in the benzo wacker) came over at a cozy 185C (28.5" Hg vac), looking and smelling as normal as ever. However, he says that just looking at it in the receiving flask, it seems to be a lower yield than he recalls with DMF. The distillation was rough going in general, he says, with much flucuation and bizarre temperature behavior (not directly attributable to chemist error). Distilling the ketone is a bitch, kids. Slow and demanding, it is... So anyway, as much as I loved Hellman's poetry (thanks Hellman, very nice!), I thought someone might like to read an unequivocal "YES" to the question of whetehr IPA could be used instead of DMF. I daresay though that the results appear to be a little less spectacular with IPA, but hey, it's good to know tht one can plow ahead and do their wacker if they have IPA but no DMF on hand and don't want to wait. I will file one more report in this thread after AGIDK reduces this ketone to the desired product, but I have no doubt that it will be fine. cheers, |
| ketone Member |
posted 10-13-1999 01:10 PM
Kids...use MeOH and let the fucker reflux. -k |
| Semtex
Enigma Member |
posted 10-13-1999 05:09 PM
Ketone, use Hushmail and let the fucker answer some mail... 
Could you drop me a line or talk to Bright Star, I think there is
something you'd like to hear about... hehehe... GRiN...
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| Osmium Member |
posted 10-14-1999 03:16 AM
Come on, Semtex, we want to know it, too! 
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| Semtex
Enigma Member |
posted 10-14-1999 08:33 PM
Osmium, didn't you get your invitation?!? Oh that's right, you never gave me your damn email so I never sent it to you, just kidding... But seriously Os, if your interested send me your PGP key mine is below, BTW send it to Semtex_Enigma@hushmail.com Yes I am aware that two layers of protection(PGP and Hushmail) are a
little extravagant, BUT hey, don't you remember, i'm the big spender...
Hey that rhymes(sp?)... Or you could just as Rhodium, i'm sure he'd tell ya... GRiN... -----BEGIN PGP PUBLIC KEY BLOCK----- mQGiBDaS6doRBADZEA4kwlgq01kn9pyKpJ6WbY5rziTIjKCOh20Us6vcjv3BMTU3 |
| Xerxes Member |
posted 10-14-1999 09:39 PM
jesus, when did PGP sigs become longer than the message content? what is that, a 1M-bit key? |
| hellman Member |
posted 10-14-1999 10:14 PM
to Methyl, YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES, YES,YES,YES,YES,YES,YES,YES,YES.SUCCESS!
Yes, IPA is a good substitute,
14/10/99 hellman |
| Semtex
Enigma Member |
posted 10-15-1999 04:26 AM
Why is it that some messages become too wide for my display, like this one has? Almost all of them are fine, cept for a few which are formatted wider...? |
| Osmium Member |
posted 10-15-1999 04:54 AM
Because Mr Hellman typed YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES,YES, without any spaces between the YESses |
| hellman Member |
posted 10-15-1999 10:29 PM
In hindsight, I would of preffered 'not that effect'
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| MaDcHeM Junior Member |
posted 10-18-1999 06:05 PM
#1-if one was not using benzoquinone and simply pumping pure O2 into the mix (like meth#1 from TS2) would there be any problems using IPA in this case? #2-could acetonitril be used in this method insted of dmf |
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