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Natural Science Forum / Chemistry / Organic Synthesis / December 2003



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HOW to synthese "4-chloro-3,5-dimethylphenol"??? thanks!!!

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gogo - 09 Dec 2003 16:48 GMT
well, how to get "4-chloro-3,5-dimethylphenol" from benzene or
1,3-dimethylbenzene? thanks to everyone who can help me on it.

email to ironmouth@263.net
with title: symthesis approach!
thank u!
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Paul J. Franklin(moderator - sci.chem.organic.synthesis)
http://organicworldwide.net/sci.chem.organic.synthesis
Georgia State University <chepjf@panther.gsu.edu>
Atlanta, GA

Uncle Al - 12 Dec 2003 18:10 GMT
> well, how to get "4-chloro-3,5-dimethylphenol" from benzene or
> 1,3-dimethylbenzene? thanks to everyone who can help me on it.
>
> email to ironmouth@263.net
> with title: symthesis approach!
> thank u!

You have some really big steric troubles there.  I'd start with
2,6-dimethylaniline, introduce the para-OH, then diazotize and
Sandmeyer.  Looks ugly.

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Paul J. Franklin(moderator - sci.chem.organic.synthesis)
http://organicworldwide.net/sci.chem.organic.synthesis
Georgia State University <chepjf@panther.gsu.edu>
Atlanta, GA

LOUIS - 23 Dec 2003 21:18 GMT
para NH2-C6H4-NO2 + 2CH3-Cl + AlCl3 --> NH2-C6H2(-CH3)2(-NO2)

NH2-C6H2(-CH3)2(-NO2) + HNO2 + CuCl ---> Cl-C6H2(-CH3)2(-NO2) + H2O + N2
+ Cu(2+)

Cl-C6H2(-CH3)2(-NO2) + Sn + HCl ---> Cl-C6H2(-CH3)2(-NH2)

Cl-C6H2(-CH3)2(-NH2) + HNO2 + H3PO3 (or EthOH) --reflux-->
Cl-C6H2(-CH3)2(-OH)

Ph Z

> well, how to get "4-chloro-3,5-dimethylphenol" from benzene or
> 1,3-dimethylbenzene? thanks to everyone who can help me on it.
>
> email to ironmouth@263.net
> with title: symthesis approach!
> thank u!

Signature

Paul J. Franklin(moderator - sci.chem.organic.synthesis)
http://organicworldwide.net/sci.chem.organic.synthesis
Georgia State University <chepjf@panther.gsu.edu>
Atlanta, GA

 
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