Thechemguuy
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Solvents for Alkylations
Hi,
I would like to do the alkylation reaction of the potassium salt of 2-hydroxy 5-methoxybenzaldehyde like mentioned in example 5 of this paper https://www.thevespiary.org/rhodium/Rhodium/chemistry/25-dim...
My problem is I don’t have Acetone at hand and that is the solvent used in this reaction.I have Isopropanol,Benzene,DMSO,Toluene,DMF,Chloroform And
Diethylether on Hand.Does anyone of you know what I could use?Also they don’t use Potassium Carbonate in the 5 Example and in example 7 the use
Ispropylalcohol which I have but tetrabutylammonium bromide instead of a carbonate which I don’t have.
Hope someone can help me.I would appreciate it
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Sigmatropic
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What you are looking for are polar aprotic solvents.
DMF and DMSO are part of this category. Acetone and acetonitrile too, but they are more reactive (=more by products) but volatile which means they
can be more easily removed after the reaction. There are a range of others such as NMP, DMA, TMU, DMPU, DMPI and HMPA but these are usually avoided
due to cost and toxicity.
Give toluene a try if you want but it may or may not work without a phase transfer catalyst (some crown ether or a quantenary ammonium salt).
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unionised
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Am I the only one puzzled by a world where 2-hydroxy 5-methoxybenzaldehyde is available, but nail varnish remover isn't?
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Elrik
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I'm frightened by a world where someone that apparently cant safely make acetone from vinegar and limestone, or even distill nail varnish remover,
will try to reflux dimethyl sulfate in acetone!
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carbchemist
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We always use DMSO and DMF.
Easy to get high grade and dry solvent.
[Edited on 26-1-2019 by carbchemist]
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