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Author: Subject: anyone have experience forming grignards from chlorobenzene
draculic acid69
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[*] posted on 12-5-2022 at 02:12


If you think water is getting into the reaction thru the drying tube
using a one-way valve might be better at keeping inside dry.
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draculic acid69
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[*] posted on 12-5-2022 at 02:21
While we're here I'm Gunna ask about this


Seen this in the benzene thread but got no response so:

p-dichlorobenzene + AlCl3 gives mostly a mix of the dichlorobenzene isomers, the chlorines seem happy to hop about on the ring but don't like to jump rings.

Does anyone know about this? Is it true? If anyone has any information on this is like theto see it Bcoz I'd like to know how grignards go with these 1,4 & 1,2 cloro benzenes also there OTCness would simplify getting grignard ingredients to practice on

[Edited on 12-5-2022 by draculic acid69]
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AvBaeyer
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[*] posted on 12-5-2022 at 08:35


Grignard reagent from chlorobenzene:

Jezierski, Roczniki Chem., 20, 47-53 (1946); Chem. Abstr. 42, 1910 (1948)

The Grignard was was formed by the entrainment method using bromoethane. The yield was 39% based on reaction with CO2 to form benzoic acid.

This reference was found in Kharasch and Reinmuth, "Grignard Reactions of Non-Metallic Substances" - a most useful reference book. It is the only report of chlorobenzene use in the entire volume of 1384 pages.

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SWIM
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[*] posted on 12-5-2022 at 14:57


I spent some time trying to form Grignards from 1,4 dichlorobenzene a while back.

Didn't have any luck but my magnesium was iffy and I didn't bother to get better stuff.

It's annoying to work with because of the mothball odor, which gets into everything.
I'm sure I was the terror of the local moth population for a while there.

I was using molten PDCB to see if the higher temperature would force a reaction. (no autoclave )






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draculic acid69
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[*] posted on 12-5-2022 at 15:59


Quote: Originally posted by SWIM  
I spent some time trying to form Grignards from 1,4 dichlorobenzene a while back.


Maybe it also needs thf to initiate.
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[*] posted on 12-5-2022 at 20:09


Yeah, could be. I didn't try too many things to make it work as it was just a screwing around to find something to do with PDCB.

The idea of doing it without solvent also attracted me from a safety standpoint, but was awfully speculative.










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