German
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Need help with a workup after a cleavage
I added a troc group (trichloroethyl chloroformate) with 2,2,2-Trichloroethoxycarbonyl chloride as part of an N-demethylation. The target molecule
crashed out from chloroform when made so it was easy to recover. I also recovered the expected weight after dried. The problem came with cleaving it.
I cleaved the troc group in acetic acid with zinc at rt. I then added water and slowly raised the pH to 7+ with a sodium hydroxide solution. This
crashed everything out so I merely filtered it and dried it. The problem is I now have 3 times by weight of what I was expecting to have.
The sodium acetate should have washed out with the water so I don't know what else I recovered in the process. Wikipedia has the cleavage mechanism on
it's 2,2,2-Trichloroethoxycarbonyl chloride entry but I don't see what solid products would have come over. I would expect a crap ton of salts but
they would have washed out with the water when it was filtered.
Can anyone help? If I just knew what the junk was I can figure out what further workup I must do but I don't know what it could be.
[Edited on 6-4-2020 by German]
[Edited on 6-4-2020 by German]
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Metacelsus
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Try a recrystallization, perhaps? I can't give any advice more specific than that without knowing what your expected product is.
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karlos³
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Someone never worked a zinc reduction up before.
His product is full of zinc hydroxide(if it even contains the product and is not just simply the zinc he has filtered out).
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German
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Quote: Originally posted by karlos³  |
His product is full of zinc hydroxide(if it even contains the product and is not just simply the zinc he has filtered out). |
THANK YOU!!!!! Now I should be able to just dissolve the product in alcohol and leave the zinc hydroxide behind. Thanks!
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German
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EDIT: nevermind
[Edited on 7-4-2020 by German]
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morganbw
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| Quote: Originally posted by German | | Quote: Originally posted by karlos³ |
His product is full of zinc hydroxide(if it even contains the product and is not just simply the zinc he has filtered out). |
THANK YOU!!!!! Now I should be able to just dissolve the product in alcohol and leave the zinc hydroxide behind. Thanks! |
Please post on how it goes.
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