Agari
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P-Nitrophenol
I am going to perform the synthesis of P-Nitrophenol using a procedure largely based on the synthesis of P-Nitroaniline. I am wondering whether or not
the following reaction scheme would work:
First is the nitration of the acetophenone which yields P and O nitroacetophenone. After isolation of the Ortho-product comes the acid hydrolysis of
the nitroacetophenone,the acid is then neutralized with ammonium or sodium hydroxide.
[Edited on 30-12-2015 by Agari]
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NexusDNA
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Hi. You usually need peroxides or other strong oxidizers to cleave benzaldehydes and acetophenones to the phenols.
Where did you get this idea from?
Bromine, definitely bromine.
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Agari
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Quote: Originally posted by NexusDNA  | Hi. You usually need peroxides or other strong oxidizers to cleave benzaldehydes and acetophenones to the phenols.
Where did you get this idea from? |
I got the idea from the reaction scheme for the synthesis of P-nitroaniline from acetanilide
[Edited on 31-12-2015 by Agari]
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gdflp
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That's the hydrolysis of an N-acetylamine, wildly different than the cleavage of a ketone. I would recommend preparing p-nitroaniline, then
diazotizing that to form the phenol (see Org Syn for details)
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NexusDNA
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Oh ok. In the case of acetanilide it works because its the hydrolysis of an amide. You cant "hydrolyse" an acetophenone with just that, it would have
very high energy carbocation intermediates (wont happen). Search about this.
What you want for your synthesis is oxidative cleavage.
Bromine, definitely bromine.
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Agari
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| Quote: Originally posted by gdflp | | That's the hydrolysis of an N-acetylamine, wildly different than the cleavage of a ketone. I would recommend preparing p-nitroaniline, then
diazotizing that to form the phenol (see Org Syn for details) |
Can you please provide a link to the specific article of interest?
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gdflp
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Here's an example for a different regioisomer.
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CuReUS
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| Quote: Originally posted by Agari |
First is the nitration of the acetophenone which yields P and O nitroacetophenone. After isolation of the Ortho-product comes the acid hydrolysis of
the nitroacetophenone,the acid is then neutralized with ammonium or sodium hydroxide.
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you won't get significant ortho/para isomers if you nitrate acetophenone,you will get majority as meta
why don't you make p-nitrophenol from phenol itself ? there are many methods on SM using nitrate salts,catalysts (clay),and the good old
HNO2 followed by dilute HNO3 route .
[Edited on 31-12-2015 by CuReUS]
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