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Topic: synthesis of p,p' dihydroxi diphenil butane  (Read 2836 times)

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Offline AndEEDJay

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synthesis of p,p' dihydroxi diphenil butane
« on: February 10, 2013, 01:37:55 PM »
as the title says I've tried to synthesis that and I've failed a little
so I wanted to make p cresole, then chlorination

so this is my idea, explained better
but I don't really like it so much
would you tell me another good method?
what I don't really when I have to obtain the p cresol because you obtain the o isomer too, and I don't want this, I want to have it 100% pure, if you know what I mean
and sorry for asking so much
« Last Edit: February 10, 2013, 01:56:57 PM by AndEEDJay »

Offline discodermolide

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Re: synthesis of p,p' dihydroxi diphenil butane
« Reply #1 on: February 10, 2013, 01:50:37 PM »
It helps if you get your structure correct. the product you drew is
OC1=CC=C(CCCC2=CC=C(O)C=C2)C=C1

4,4'-(propane-1,3-diyl)diphenol

You actually want this structure?
OC1=CC=C(CCCCC2=CC=C(O)C=C2)C=C1

4,4'-(butane-1,4-diyl)diphenol
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Offline AndEEDJay

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Re: synthesis of p,p' dihydroxi diphenil butane
« Reply #2 on: February 10, 2013, 01:57:56 PM »
sorry, may fault
I want the second one
I modified

Offline Dan

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Re: synthesis of p,p' dihydroxi diphenil butane
« Reply #3 on: February 10, 2013, 07:13:13 PM »
I would expect acid/base reactions between the phenol and carbide to complicate this...
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Offline orgopete

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Re: synthesis of p,p' dihydroxi diphenil butane
« Reply #4 on: February 10, 2013, 09:33:38 PM »
And polymerization of phenol.
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Offline AndEEDJay

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Re: synthesis of p,p' dihydroxi diphenil butane
« Reply #5 on: February 11, 2013, 12:25:57 PM »
and finally what is the answer?

Offline orgopete

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Re: synthesis of p,p' dihydroxi diphenil butane
« Reply #6 on: February 11, 2013, 12:30:05 PM »
You need protection-deprotection or another route, such as acylation-reduction.
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Offline AndEEDJay

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Re: synthesis of p,p' dihydroxi diphenil butane
« Reply #7 on: February 11, 2013, 12:55:53 PM »
would you tell me a correct way to synthesis that?
without secondary products, with high yield..

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