DraconicAcid
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Purple Oil....
In my organic chemistry class, we do a t-butylation of bipphenyl using ferric chloride and t-butyl chloride in dichloromethane. I'm trying to get
away from using halogenated organic crap in the lab, so I thought I'd look into replacing this lab.
So I tried alkylating biphenyl directly with t-butanol and sulphuric acid (using acetic acid as a solvent, because it worked for some other
alkylations). A literature search gave me lots of examples of zeolite-catalyzed alkylations, but I don't have a shelf full of zeolite to pick and
choose from.
I got a frikkin purple oil. Purple. Yellow would not have at all suprised me, but purple?
Any ideas what could have given me the purple, dichloromethane-soluble oil?
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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Texium
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What does it look like by TLC? Usually when I get a weird color like that, it’s a strongly colored minor product and the bulk of the material is
actually colorless or yellow. If you can get it to separate on TLC and see a separate non-purple spot that’s strongly UV active, then that’s
probably the case. And then maybe you could column purify it and isolate the purple stuff.
Also, side note, we have a nice Friedel-Crafts lab where the students run an intramolecular acylation with phenylbutyric acid and methanesulfonic
acid to make alpha-tetralone. It works really well and makes a pretty neat product.
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DraconicAcid
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I've been meaning to run a TLC, but I've been doing too many things at once.
Could you send me the write-up for your tetralone experiment? I'm a bit restricted reagent-wise, but it would be interesting to see. (Too bad I
can't use a similar procedure to make indenone- we have lots of cinnamic acid.)
I also tried t-butylation of salicylic acid according to this guy's method:
https://etheses.whiterose.ac.uk/id/eprint/14177/1/338622.pdf
I got a mixture of white crystals and an oil which eventually solidified. Trying to recrystallize it from isopropanol/water with a small amount of
hydrochloric acid gave a nice colourless liquid. No frikking idea what that is.
[Edited on 28-2-2025 by DraconicAcid]
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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