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Topic: Turbo Grignards - Any expertience out there?  (Read 1291 times)

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Offline AlphaScent

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Turbo Grignards - Any expertience out there?
« on: May 02, 2022, 03:58:15 PM »
Trying to make the Grignard of cyclopropylmethyl chloride (CPMC) using a turbo Girgnard (iPrMgCl*LiCl) approach to form the Grignard of CPMC.  Then we want to treat with CO2 to form the carboxylic acid.  That is an intermediate we need.  Also, I have always seen this done with solid CO2 (dry ice), has anyone done this by pumping CO2 gas into the reaction?  I assume residence time in the reaction is not long enough this way? 

We work on KG scale so making the Grignard with Mg is not practical.  Has anyone ever used it to successfully form the Grignard of a primary alkyl halide?  If so, what temp did you run?

I have not consulted the literature yet, doing it now.

Thanks in advance!

Cheers,

Bob
If you're not part of the solution, then you're part of the precipitate

Offline rolnor

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Re: Turbo Grignards - Any expertience out there?
« Reply #1 on: May 02, 2022, 05:16:03 PM »
You can use 3eqv. 1,2-dichloroethane and 4 eqv. Mg to  the make the Grignard. The dichloroethane is converted to ethylene.This way you get a very activated magnesium. You can also use potassium metal+magnesium chloride in THF, you get extremely reactive magnesium, finely divided. Then add the chloride. This magnesium will even convert fluorobenzene to phenylmagnesium fluoride. This is called Rieke metal.

https://en.wikipedia.org/wiki/Rieke_metal

Offline kriggy

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Re: Turbo Grignards - Any expertience out there?
« Reply #2 on: May 03, 2022, 07:38:38 AM »
We prepared bicarbonate from gas CO2 in undergrad, I assume you can pump it through the reaction if you have suitable setup, its gas so it either reacts and then leaves. I see no issue with that.
We did benzoic acid from solid CO2 but that was probably mainly due to having easy acces to solid CO2.

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