dormouse (Member)
04-25-00 00:04
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      Synthesis of Toluene-hydroquinone? -psychokitty  Bookmark   


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Author  Topic:   Synthesis of Toluene-hydroquinone? 
Synthesis of Toluene-hydroquinone? 
psychokitty
Member   posted 11-04-1999 06:42 PM          
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This question is primarily aimed at Rhodium.
Just wondering if the proceedure detailed in an article I found published in JACS vol. 65, 1943, pp.1431-1432 titled "Some Derivatives of Creosol" has any application in the synthesis of 4-methyl-2,5-(dimethoxy) allylbenzene, a potential precursor to DOM.

Basic outlined scheme is as follows:

1. Formation of the benzaldehyde from the methoxy-hydroxy benzene.

2. Conversion of aldehyde via the Clemmensen reduction into the hydroxy-methoxy-toluene.

3. Formation of the methoxy-methyl allyl-phenol ether from the hydroxy-methoxy-toluene and allylbromide.

4. Claisen rearrangement of the methoxy-methyl allyl-phenol ether into the allyl-hyroxy-methoxy-methyl-benzene.

5. Methylation of the phenolic group to form the desired allyl-dimethoxy-methyl-benzene.

Don't know if I generallized the shit out of my intermediates to where no one can imagine what they look like, but I did my best.

Rhodium, would this work?

--PK


psychokitty
Member   posted 11-04-1999 06:48 PM          
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This is fucked up. I was originally going to name the thread as it presently is, but then through the course of writing the contents of it, I knew that such a title made no sense so I decided to rename the thread "Synthesis of 4-Methyl-1-(2,5 dimethoxy)-allylbenzene" but I forgot to make the modification.
Sorry.

--PK


Rhodium
Administrator   posted 11-06-1999 07:12 PM          
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Yes, that sounds like a viable idea. Try it!
 
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