What happens when butan-2-ol reacts(under heat) with $\ce{CH3COCl}$ in the presence of pyridine? Does it form $\ce{CH3COOCH(CH3)CH2CH3}$? I got the ester mentioned but the solution says it gives an alkene. What is the product when an alcohol reacts with an acid chloride in the presence of pyridine?

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    $\begingroup$ How much pyridine and at what temperature? $\endgroup$
    – Waylander
    Jun 4 at 11:24
  • $\begingroup$ These are standard acylation conditions for alcohols done at ice-bath or room temperature, so unless it is being heating strongly in the presence of a large excess of pyridine I doubt you're going to get an alkene. What is the source that says you will? $\endgroup$
    – Waylander
    Jun 4 at 12:22
  • $\begingroup$ @Waylander The amount of pyridine is not mentioned but the the reaction proceeds under heating. $\endgroup$
    – Boson
    Jun 4 at 13:01
  • $\begingroup$ In what solvent at what temperature? $\endgroup$
    – Waylander
    Jun 4 at 14:00

I found that the reaction you describe is a special form of the Schotten-Baumann reaction.

The special form of the reaction is called Einhorn-Acylierung ("Unicorn acylation" in English). It is named after the chemist Albert Einhorn (Einhrorn means "unicorn" in German and hence the reaction name).

The reaction mechanism is as follows:

First, the pyridine forms an acetyl pyridinium salt. The alcohol can then perform a nucloephilic attack. The pyridine gets removed and can remove one hydrogen to reach the final product.

Einhorn Acylation CC BY-SA 4.0

Image source: From the German Wikipedia article


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