Conversion of alcohols to alkyl chlorides using SOCl2
Description: Primary or secondary alcohols can be converted into alkyl chlorides through treatment with SOCl2.
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Real-Life Example:
Org. Synth. 1945, 25, 84
DOI Link: 10.15227/orgsyn.025.0084
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Hello 🙂, I wonder why chloride ion attacks carbon in step 3 in the mechanism of this reaction, while in step 3 in the mechanism of formation of tosylates from alcohols chloride ion attacks H? thanks.
Hi,
why is this reaction usually carried out in pyridine or a tertiary amine?
The purpose of the tertiary amine is to neutralize any HCl that is formed during the reaction. [Pyridine can also displace Cl from SOCl2 to give SOCl(pyr+) which has a better leaving group, but that’s a detail I didn’t want to go into].