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Topic: 3-Acetyl-2,5-Dimethylfuran: Polar Aprotic Solvent?  (Read 2920 times)

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Offline HailoMan

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3-Acetyl-2,5-Dimethylfuran: Polar Aprotic Solvent?
« on: January 11, 2012, 03:03:06 PM »
Hi all,

Just wondering if 3-acetyl-2,5-dimethylfuran would make a good polar aprotic solvent?
I try to find reference for its use as solvents, but I can only seem to find its use as an intermediate compound.
Does it suggest that it is highly reactive? (Other than the fact that it's unsaturated, I can't explain why it would be reactive though, considering that a ketone tends to be less reactive compared to an aldehyde or alcohol group).

I notice that a lot of compounds with furan ring seems to be alright solvents, but the most common ones are protic solvents, e.g. furfural or furfuryl alcohol.
I am trying to find a furan-derivative to use as high boiling point aprotic solvent.
Any suggestions?

Offline discodermolide

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Re: 3-Acetyl-2,5-Dimethylfuran: Polar Aprotic Solvent?
« Reply #1 on: January 11, 2012, 03:06:54 PM »
Hi all,

Just wondering if 3-acetyl-2,5-dimethylfuran would make a good polar aprotic solvent?
I try to find reference for its use as solvents, but I can only seem to find its use as an intermediate compound.
Does it suggest that it is highly reactive? (Other than the fact that it's unsaturated, I can't explain why it would be reactive though, considering that a ketone tends to be less reactive compared to an aldehyde or alcohol group).

I notice that a lot of compounds with furan ring seems to be alright solvents, but the most common ones are protic solvents, e.g. furfural or furfuryl alcohol.
I am trying to find a furan-derivative to use as high boiling point aprotic solvent.
Any suggestions?

I've never used it but I would hazard a guess that the acetyl group might interfere in a lot of chemistry. Ideally the solvent should be inert to the reaction conditions.
Try sulfolane
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Offline Doc Oc

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Re: 3-Acetyl-2,5-Dimethylfuran: Polar Aprotic Solvent?
« Reply #2 on: January 11, 2012, 05:52:21 PM »
Acylfurans are generally very expensive and, as discodermolide pointed out, the acetyl group will likely interfere with a lot of chemistry you're trying to do.

Why do you have to use a furan?  There are lots of high boiling polar aprotic solvents available that are very cheap.  Dioxane and DMF come to mind immediately.  You could resort to DMSO, but it's one of the worst to get rid of so I try to avoid it at all costs.

Offline HailoMan

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Re: 3-Acetyl-2,5-Dimethylfuran: Polar Aprotic Solvent?
« Reply #3 on: January 12, 2012, 12:12:51 AM »
Thanks for the input.
Trying to find a polar aprotic solvent that can be synthesised from renewable sources and furan groups seem like an obvious choice given that you can obtain its derivatives from fructose.

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