j_sum1
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Precursors to um… something. Suggestions invited.
I have recently acquired a bunch of seemingly interesting reagents. (Back story follows later). I am wondering what I might use them for.
My restrictions are these: I am no OC guru. I have little practical experience but I do have some basic glassware and some standard solvents as well
as a few alcohols and organic acids. I am wanting syntheses that I can perform with these reagents that are
Straightforward for someone of my limited experience
Can be expected to have reasonable yields without hideous workups
Preferably involving a mechanism that is well known and which is to not too difficult for me tounderstand.
Product that is either useful for something else or has distinctive / interesting properties – can be identified without sophisticated
analytical equipment
Here is my list of reagents:
Propylamine
diethylene glycol monoethyl ether (2-(2-Ethoxyethoxy)ethanol)
n butyl acetate
1-bromonaphthalene
2-ethoxyethyl acetate (ethylene glycol monoethyl ether acetate)
2-chlorobenzaldehyde
2,4,6 collidine (2,4,6 trimethyl pyridine)
And now for the back story.
The other day I had the wonderful opportunity to meet up with a fellow SM member, Lion850. He had purchased a few chems in bulk and was happy to sell
some of his surplus. But he had the previous day visited a local supplier and had saved a pile of organics from being discarded. You probably know
Lion's nice work on inorganic salts (beautiful collection) but he really has no interest in OC at this stage. So he passed the pile on to me.
I would love some project ideas...
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B(a)P
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If you are having issues in the classroom you could convert 2-chlorobenzaldehyde to 2-chlorobenzalmalononitrile for crowd control purposes 
Sorry, not much help, I am generally rubbish with OC.
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draculic acid69
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The trimethyl pyridine could be turned into the hydrochloride and if it's as hygroscopic as pyridine HCL it'll absorb enough water to basically
dissolve itself. The clorobenzaldehyde can be weighed per ml (density tested) then could be refluxed with sodium iodide in acetone precipitating salt
and changing in density per ml(theoretically, not sure of side reactions). The bromonapthalene could make a grignard with mg in ether or an alcohol
could be formed with a hydroxide or a napthylpropylamine can be made with propylamine and the bromonapthalene.
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draculic acid69
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The glycols and ester can be hydrolyzed into acids and alcohols
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mackolol
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If you will be able to get 2 amino phenol, you can make dibenzoxazepine (CR tear gas) with your 2 chloro benzaldehyde, which is an interesting and
veery potent lachrymator.
You can also substitute pyridine for trimethylpyridine in various reactions and check if it is better, for example demethylation of compounds or maybe
is synthesis of this copper triphenylphosphine and pyridine triboluminescent complex.
[Edited on 2-7-2020 by mackolol]
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Metacelsus
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Quote: Originally posted by draculic acid69  | | The clorobenzaldehyde can be weighed per ml (density tested) then could be refluxed with sodium iodide in acetone precipitating salt and changing in
density per ml(theoretically, not sure of side reactions). |
I don't think this will work; iodide won't displace chlorine from an aryl ring under these conditions.
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njl
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I think the solubility is what would be driving the reaction forward so the thermodynamics aren't as important
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Tsjerk
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| Quote: Originally posted by njl | | I think the solubility is what would be driving the reaction forward so the thermodynamics aren't as important |
Normally this reaction is driven by the fact NaCl is not soluble in acetone indeed... but if the chlorine doesn't leave, you can stir what you want,
but you won't get any NaCl.
[Edited on 2-7-2020 by Tsjerk]
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draculic acid69
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Do you know what the reason it won't work is? I'm curious as to whether this is a thing with aryl compounds in general or whether the aldehyde is
affecting it. I was going to try the sodium iodide displacement on some dichlorobenzene but if it ain't going to work I'll scrap that idea.
[Edited on 4-7-2020 by draculic acid69]
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Tsjerk
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Aryl halides bonds are strong compared to alkyl halide bonds, this is because of the resonance in the backbone, making the carbocation less stable.
An electonegative group like for example a nitro group in a ortho or para position would stabilize the carbonation, but the aldehyde not so much.
This is also the reason why tertbutyl chloride, 2-chlorobutane and 1-chlorobutane react in descending order, this is because of the stability of the
cation and therefore the leaving power of the chlorine.
[Edited on 4-7-2020 by Tsjerk]
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clearly_not_atara
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You may be able to make 2-methylbenzoxazole by the following sequence of reactions:
ethoxyethyl acetate + ammonia >> acetamide + ethoxyethanol (interesting in itself)
acetamide + 2-chlorobenzaldehyde + CuI (catalyst) + 2,4,6-collidine (ligand) >> 2-formylacetanilide (Goldberg reaction)
2-formylacetanilide + H2O2 + NaOH >> 2-hydroxyacetanilide (Dakin reaction, unsure about amide stability)
2-hydroxyacetanilide - H2O (heat? H2SO4? HPO3?) >> 2-methylbenzoxazole
It's not the most interesting compound I know of, but apparently has a distinctive smell. It may form a methiodide. The Goldberg reaction is the most
interesting thing I saw in the reagents you have.
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draculic acid69
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Could try demethylation of vanillin with the trimethyl pyridine HCL
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