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Master Organic Chemistry Reaction Guide

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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3 thoughts on “Conversion of alcohols to alkyl chlorides using SOCl2

  1. 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.

    1. 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].

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