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Author: Subject: Methylation with sodium methyl sulfate?
Douchermann
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[*] posted on 11-8-2009 at 18:41
Methylation with sodium methyl sulfate?


I recently came across a thread which I thought was here on SM that entailed the methylation of phenols with sodium methyl sulfate or methyl hydrogen sulfate. I have searched for about 45 minutes now. I know orgsyn has also referenced this, I've got the quote in front of me, but I can't find the specific page. Could anyone point me in the correct direction?



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kclo4
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[*] posted on 12-8-2009 at 02:30


http://www.orgsyn.org/orgsyn/prep.asp?prep=CV1P0058

The references at the bottom should be useful, and I believe this is the page you are looking for?




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Douchermann
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[*] posted on 12-8-2009 at 10:08


Yes, thats the orgsyn page. Would anyone be able to get me the following article now?
JACS, 1914, 36, pages 1885–1891




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kclo4
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[*] posted on 12-8-2009 at 11:09


I too would be interesting in seeing this article.



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DJF90
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[*] posted on 12-8-2009 at 11:42


There seems to be some confusion about this article. It regards the distillation of the alkali phenolate with the alkali alkyl/aryl sulfonate to make the phenyl ether. I will post the article later when I have the time.
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[*] posted on 12-8-2009 at 13:17


Also # Aktien-Gesellschaft für Anilin-Fabrikation, Ger. pat. 23,775 [Frdl. 1, 43 (1877–87)].
from the same orgsyn page looks pretty interesting, claims to use methyl alcohol and potassium bisulfate. I figure that would be just as useful to you.




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S.C. Wack
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[*] posted on 12-8-2009 at 14:47


UTFGoogle Books for the JACS article and most others from 1879-1922. You will see that it says sodium methylsulfonate. The error of OS online is not in the original volume, which is also highly available yet unread.

The authors in the JACS article did however obtain their methylsulfonic acid from methylsulfuric acid, via sulfite. They do not say how well DE55007 works but it apparently does.

EDIT: The method in the patent was also published in Berichte der etc. in the same year, 1890: http://gallica.bnf.fr/ark:/12148/bpt6k90720c.image.r=Bericht...

[Edited on 12-8-2009 by S.C. Wack]
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Vogelzang
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[*] posted on 14-8-2009 at 06:24


http://www.sciencemadness.org/talk/viewthread.php?tid=1261&a...

http://v3.espacenet.com/publicationDetails/originalDocument?...

[Edited on 14-8-2009 by Vogelzang]
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