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Author: Subject: Different possible products of reaction of alcohol with SOCl2
teodor
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[*] posted on 19-7-2021 at 03:19
Different possible products of reaction of alcohol with SOCl2


I try to understand the reaction of alcohol with SOCl2. I can see that depending on conditions it would be either alkyl chloride or sulfite ester. It seams that in both cases the intermediate product is chlorosulfite ester. The question is, what is the mechanism of the alkyl chloride formation and how it is different from sulfite ester formation, in other words, which conditions are essential to shift the reaction to one of 2 possible directions?
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rockyit98
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[*] posted on 19-7-2021 at 05:20


SOCl2 is used to make when you need pure products since SO2 and HCl will bubble off as a gas mix, so no post processing.it can also used to dry premade alkyl chloride and acyl chlorides even hard to dry metal chlorides such as AlCl3 , ZnCl2 .



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teodor
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[*] posted on 19-7-2021 at 05:39


Quote: Originally posted by rockyit98  
SOCl2 is used to make when you need pure products since SO2 and HCl will bubble off as a gas mix


I suspect some of SO2 and HCl will not bubble off but will stay bounded and we always can get a mix of chloride and sulfite esters as a general case. Also SOCl2 can undergo decomposition to different products during the reaction depending on the temperature. Also some alcohols start decomposition reacting with SOCl2, so I suspect the catalysers like pyridine are used for a good reason.
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teodor
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[*] posted on 19-7-2021 at 07:14


OK, I found some answers to my questions here: https://sci-hub.se/https://doi.org/10.1021%2Fcr60226a001
But I still have impression of some magic, because according to the article it depends even on the order of mixing.
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