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Is SOCl2 needed?

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rentj:
Is the first step of adding SOCl2 needed for this synthesis? Because the excess LAH in the second step will do the same thing, which is producing a primary alcohol. Thank you

Babcock_Hall:
I am not sure what would happen if you left out the thionyl chloride.  If you are following a literature preparation, I see no reason to deviate from it.

Hunter2:
I think with the Thionylchloride you create first the cyclopentylcarboxylchloride, this should be reduced to the aldehyde to obtain in the end the Acetale. If you get total reduction to the cyclopentylmethanol then it is not possible to fo further.

rolnor:

--- Quote from: Hunter2 on May 01, 2024, 03:33:29 PM ---I think with the Thionylchloride you create first the cyclopentylcarboxylchloride, this should be reduced to the aldehyde to obtain in the end the Acetale. If you get total reduction to the cyclopentylmethanol then it is not possible to fo further.

--- End quote ---

But there is PCC in the reagent list, do you know what that is for? Can you reduce an acid chloride to aldehyde with LAH?

Hunter2:
It's an oxidiser. To oxidise Alkohol to Aldehyde. Yes with LAH the Reduction goes direction to the Alkohol.
But if so then LAH can be used to refuse the carbonic acid. Maybe SOCl2 is only used to remove water.

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