markymark25
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4-Propylaniline - (2696-84-6) Synthesis
Does anyone have a synthesis for 4-Propylaniline
(2696-84-6)
We want to produce around 500g - 1kg and are having trouble synthesising it.
Our subtracted chemist ran it yesterday and it quickly became clear that the constituents have to be heated together under pressure. This became clear
at around 200C whilst desperately trying to keep n-Propanol (bp around 95C) and Aniline (bp around 190C) in the flask - target temperature around
280C. The other component here is Zinc Chloride (anhydrous) - masses of it - so the whole batch mixture was a bit like freshly vomited lava with a
return stream of exploding condensate.
Similar type reactions with Aluminium Chloride (eg Diels Alder) often form a complex which is a fully mobile lower melting eutectic mixture - but
thatwas not the case here.
Any suggestions?
Thanks in advance
Mark
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Bolt
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Yes - obviously, you need pressure. Please [include] references with each post.
You could try a reductive alkylation (I've never checked to make sure the strategy works with aryl amines, but I assume it will since it works for the
n-alkylation of some amides) or use a carbamate protecting group (e.g., t-boc) and use a base (e.g., 50% NaOH) + an alkylating agent (e.g., dialkyl
carbonate or alkyl halide) + a PTC for anionic reactants (isn't necessary, rxn time and yeilds will be a lot better) then deprotect.
If you're looking for a more economical, safer, less messy rxn check the patent lit.
[Edited on 17-11-2010 by Bolt]
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Sedit
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Explain who WE is please.
Knowledge is useless to useless people...
"I see a lot of patterns in our behavior as a nation that parallel a lot of other historical processes. The fall of Rome, the fall of Germany — the
fall of the ruling country, the people who think they can do whatever they want without anybody else's consent. I've seen this story
before."~Maynard James Keenan
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markymark25
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Thank you for your responses!!
Mark
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