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Author: Subject: Precursors to um… something. Suggestions invited.
j_sum1
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[*] posted on 1-7-2020 at 16:44
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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    [*] posted on 1-7-2020 at 21:32


    If you are having issues in the classroom you could convert 2-chlorobenzaldehyde to 2-chlorobenzalmalononitrile for crowd control purposes :D
    Sorry, not much help, I am generally rubbish with OC.
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    draculic acid69
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    [*] posted on 1-7-2020 at 21:54


    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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    [*] posted on 1-7-2020 at 21:58


    The glycols and ester can be hydrolyzed into acids and alcohols
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    mackolol
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    [*] posted on 2-7-2020 at 03:19


    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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    [*] posted on 2-7-2020 at 04:31


    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.




    As below, so above.
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    njl
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    [*] posted on 2-7-2020 at 07:01


    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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    [*] posted on 2-7-2020 at 07:59


    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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    [*] posted on 4-7-2020 at 05:19


    Quote: Originally posted by Metacelsus  

    I don't think this will work; iodide won't displace chlorine from an aryl ring under these conditions.


    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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    [*] posted on 4-7-2020 at 06:58


    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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    [*] posted on 4-7-2020 at 08:54


    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.




    [Edited on 04-20-1969 by clearly_not_atara]
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    draculic acid69
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    [*] posted on 4-7-2020 at 18:26


    Could try demethylation of vanillin with the trimethyl pyridine HCL
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