Filemon
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Chlorination with CuCl2
How is the reaction?
Acetone + 2 CuCl2 => chloroacetone + 2 CuCl + HCl?
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Baphomet
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External heat is required and the reaction is performed in DMF with LiCl as catalyst. See C.E. Castrol et al. in The Journal of Organic Chemistry,
vol30 (1965) pp587
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solo
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Reference Information
Cupric Halide Halogenations
C. E. CASTRO, E. J. GAUGHAN, AND D. C. OWSLEY
Journal of organic chemistry 1965, vol:30, iss:8, pg:2493
Abstract
Cupric bromide and cupric chloride in refluxing methanol and higher alcohols effect the following transforma- tions : p-alkoxylation a-halogenation
of carbonyl-conjugated vinyl groups, halogenation of isoleted double bonds, trans halogenation of internal acetylenes, and trihalogenation
of terminal acetylenes. In a reaction of undefined scope, ethanol is oxidatively halogenated with cupric bromide to dibromoacetaldehydediethyl
acetal. Kinetics of some representative transformations have been examined. Cupric bromide but not cupric chloride functions as a source of low
concentrations of halogen. Mechanisms for some of the conversions are suggested.
Attachment: Cupric Halide Halogenations.pdf (704kB)
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Nicodem
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| Quote: | Originally posted by Filemon
How is the reaction?
Acetone + 2 CuCl2 => chloroacetone + 2 CuCl + HCl? |
This has already been discussed and explained in another thread. UTFSE before asking old questions and opening new threads!
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guy
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why is LiCl used as catalyst? What is it's mechanism?
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JohnWW
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It probably forms some sort of double salt, like Li2CuCl4.
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guy
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| Quote: | Originally posted by JohnWW
It probably forms some sort of double salt, like Li2CuCl4. |
Edit:
Acutally, LiCl is quite soluble in acetone, providing a source of soluble chloride ions to increase the rate.
[Edited on 12/3/2006 by guy]
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Nicodem
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https://sciencemadness.org/talk/viewthread.php?tid=2713&...
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Ephoton
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you should add peroxide to that mix it will give you a 78% yeild and the lithium is not nessacery plus it cost too much.
e3500 console login: root
bash-2.05#
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guy
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| Quote: | Originally posted by Ephoton
you should add peroxide to that mix it will give you a 78% yeild and the lithium is not nessacery plus it cost too much. |
Really? So add some H2O2 to the mixture?
What is the mechanism for that?
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Ephoton
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sorry my mistake I missed out a reagent in my hast  also needed is hydrochloric
acid
then this can be done wet as well. and the yield will be a bit lower than 78% sorry.
reflux 5 hours done. ratio is 2:1:1.3 tone acid peroxide only small amounts of copper are needed as a catylist sorry my mistake. still think its the
way to go though.
will post full refs when the time is right.
e3500 console login: root
bash-2.05#
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