Preparation of acyl chlorides
المؤلف:
University of Missouri System
المصدر:
Organic Chemistry ii
الجزء والصفحة:
.................
21-10-2020
2367
Preparation of acyl chlorides
This page discusses the methods of swapping the -OH group in the -COOH group of a carboxylic acid for a chlorine atom to make acyl chlorides (acid chlorides) using thionyl chloride. In the examples below, consider the conversion of acetic acid to acetyl chloride to be typical of these types of reactions.
Thionyl chloride is a liquid at room temperature and has the formula SOCl2
. It reacts with carboxylic acids to produce an acyl chloride, giving off sulfur dioxide and hydrogen chloride gases. For example:
CH3COOH+SOCl2→CH3COCl+SO2+HCl
The separation is simplified to an extent because the by-products are both gases. Fractional distillation is still required to separate the acyl chloride from any excess acid or thionyl chloride.
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