<div>I am using THF as the mobile phase for HPLC so I wonder if the compound is still getting hydrolyzed. Also, if there is a better way to monitor this reaction please let me know.</div> <div>I am using this reaction to incorporate the SO<FONT size=1>2</FONT> group so the final strucutre after this reaction would be Ar-CH<FONT size=1>2</FONT>-O-SO<FONT size=1>2</FONT>Cl</div> <div>The next step I want to try is to substitute the Cl group.</div> <div> </div> <div>Regards,</div> <div>Jay<BR><BR><B><I>Andrew Lund <android109@hotmail.com></I></B> wrote:</div> <BLOCKQUOTE class=replbq style="PADDING-LEFT: 5px; MARGIN-LEFT: 5px; BORDER-LEFT: #1010ff 2px solid"><BR>Is it possible that what's happening is that the sulfuryl chloride is chlorinating the alcohol and then under the HPLC conditions this is hydrolysing back to the starting alcohol? Sulfuryl chloride is very reactive and I'd expect it toi react immediately with the alcohol. Is the chlorosulfonate the
final target or is it simply an activated intermediate where perhaps mesylate might be a better choice...?<BR>Andy<BR><BR><BR><BR><BR>________________________________<BR>> Date: Mon, 8 Jan 2007 14:29:34 -0800<BR>> From: hi_buddy03@yahoo.com<BR>> To: everybody@orglist.net<BR>> Subject: ORGLIST: chlorosulfation<BR>> <BR>> Hello all,<BR>> I am trying to perform a chlorosulfation reaction as an intermediate step.<BR>> The reaction is as follows:<BR>> Ar-CH2OH + SO2Cl2 --------> Ar-CH2OSO2Cl<BR>> (3 mol) (3.6mol)<BR>> Toluene as solvent and pyridine as a base.<BR>> I am monitoring this reaction on HPLC but I cannot see anything other than the starting material peak.<BR>> I thought SO2Cl2 being very reactive would give the product easily.<BR>> I need some feedback on as to whether the method that I am using for synthesis has flaws or the reaction monitoring method is incorrect?<BR>> If anybody has a new approach to this synthesis
should also be fine.<BR>> Thanks,<BR>> Jay<BR>> __________________________________________________<BR>> Do You Yahoo!?<BR>> Tired of spam? Yahoo! Mail has the best spam protection around<BR>> http://mail.yahoo.com<BR><BR>_________________________________________________________________<BR>Try amazing new 3D maps<BR>http://maps.live.com/?wip=51<BR>_______________________________________________<BR>ORGLIST - Organic Chemistry Mailing List<BR>Website / Archive / FAQ: http://www.orglist.net<BR>To post a message (TO EVERYBODY) send to everybody@orglist.net<BR>To unsubscribe, send to everybody-request@orglist.net the message: unsubscribe your_orglist_password your_address<BR></BLOCKQUOTE><BR><p> 
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