Jackson
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MeHQ from benzoquinone
Hi, I am looking to synthesize 4-Methoxyphenol from benzoquinone. My question is, Can hydroquinone be replaced with benzoquinone in the reaction? The
reaction would be an acidic benzoquinone solution in methanol reacting in a free radical reaction. Would this work at all? I would be able to get
hydroquinone, but seeing as I already have benzoquinone, it would be preferable.
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Schleimsäure
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In wikipedia it is stated:
4-Methoxyphenol is produced from p-benzoquinone and methanol via a free radical reaction.
However the given sources on that statement only show a start from hydroquinone. In one of these routes p-benzoquinone is used as a catalyst.
See also here:
http://www.sciencemadness.org/talk/viewthread.php?tid=9835
So, my guess as a layman, is no. The double bonds of the oxygens are quite different than the OH-groups of the dihydroxybenzenes.
Somebody more knowledgable than me probably can explain the mechanism.
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Jackson
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Yeah, in that thread, the reaction mechanism looks like benzoquinone is the actual thing undergoing the reaction, and it is needed to start the
reaction, because the reaction converts hydroquinone to benzoquinone.
![C8C6EA38-B478-4B03-80F0-A81279013C8D.gif - 4kB](https://www.sciencemadness.org/whisper/files.php?pid=602792&aid=73891)
PS: could other alcohols be used for this purpose like ethanol to get 4-ethoxy phenol instead?
[Edited on 2/20/2019 by Jackson]
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Tsjerk
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Quote: Originally posted by Jackson ![](images/xpblue/lastpost.gif) |
PS: could other alcohols be used for this purpose like ethanol to get 4-ethoxy phenol instead?
[Edited on 2/20/2019 by Jackson] |
Probably
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Jackson
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Okay, guess I’ll just have to try it and report back
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Jackson
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Okay, I have tried it with isopropanol and Benzoquinone.
I added about a gram of Benzoquinone to a beaker and then added 91% percent isopropanol until it all dissolved. Then I added about five ml of 96%
sulfuric acid. This was mixed for 24 hours. It was ten neutralized with sodium bicarbonate, which yielded a white precipitate. This was filtered out,
and an attempted recrystalization from naphtha was attempted. It didn’t really dissolve so I tried heating. It didn’t dissolve but it did have a
melting point within a couple degrees of the theoretical melting point. I think it might be the sodium salt of 4-isopropoxyphenol. I put it into the
freezer and it froze into a white chunk on the bottom of the flask. I took it out and put it onto some filter paper to dry.
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Nicodem
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Quote: Originally posted by Jackson ![](images/xpblue/lastpost.gif) | It was ten neutralized with sodium bicarbonate, which yielded a white precipitate. This was filtered out, and an attempted recrystalization from
naphtha was attempted. It didn’t really dissolve so I tried heating. |
Sodium sulfate decahydrate is not soluble in naphtha or similar organic solvents.
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