From: Jacob Zabicky (zabicky$##$bgumail.bgu.ac.il)
Date: Thu Feb 06 2003 - 07:52:52 EST
Dear Antonio,
The oleum is apparently needed to overcome the electronegativity of the
chloro substituent, in spite of its o,p-directing effect. Chlorosulfonic
acid has also been proposed for sulfonation, J. Stewart, J. Chem. Soc. 121,
2556 (1922), leading to the sulfonyl chloride; you may try that.
Just for kicks, a Gattermann syntheis may be attempted from
p-chloroaniline, leading to the corresponding benzenesulfinic acid, L.
Gattermann, Ber. 32, 1136 (1899); J. Thomas, J. Chem. Soc. 95, 342 (1909);
R. D. Haworth and A. Lapworth, J. Chem. Soc. 123, 2986 (1923). The sulfinic
acid may be then oxidized to the sulfonic acid by various routes.
All the best,
Jacob
At 18:20 5/2/2003, antonio regla wrote:
>Dear list members:
>
>Does anyone know of a good prep for this compound? I have tried refluxing
>p-chlorobenzene and sulfuric acid, and I still have a considerable amount
>of p-chlorobenzene after several hours reflux. I have checked Vogel's
>textbook, but they report the use of fuming sulfuric acid, which is hard
>to come by. Well, thanks for your help.
>
>Best regards.
>
>J. A. Regla
>
>
>
>---------------------------------
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><P>Dear list members:</P>
><P>Does anyone know of a good prep for this compound? I have tried
>refluxing p-chlorobenzene and sulfuric acid, and I still have a
>considerable amount of p-chlorobenzene after several hours reflux. I have
>checked Vogel's textbook, but they report the use of fuming sulfuric acid,
>which is hard to come by. Well, thanks for your help.</P>
><P>Best regards.</P>
><P>J. A. Regla</P><p><br><hr size=1>Do you Yahoo!?<br>
><a
>href="http://rd.yahoo.com/mail/mailsig/*http://mailplus.yahoo.com">Yahoo!
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Prof. Jacob Zabicky
Institutes for Applied Research
Ben-Gurion University of the Negev Private: POB 12366, Beer-Sheva 84863
POB 653, Beer-Sheva 84105, ISRAEL Tel. +972-8-6496792
http://profiler.bgu.ac.il/site/main.cfm
Tel. +972-8-6461271/6461062/6472754
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