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Acetyl chloride was first prepared in 1852 by French chemist Charles Gerhardt by treating potassium acetate with phosphoryl chloride. [4]Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as phosphorus trichloride (PCl 3), phosphorus pentachloride (PCl 5), sulfuryl chloride (SO 2 Cl 2), phosgene, or thionyl chloride (SOCl 2).
In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids (R−C(=O)OH). A specific example of an acyl chloride is acetyl chloride, CH 3 COCl.
Acylium ions are intermediates in several reactions, such as the Friedel-Crafts acylation of arenes by acetyl chloride in the presence of aluminium trichloride: C 6 H 5 R + CH 3 CO + + AlCl − 4 → CH 3 COC 6 H 4 R + HCl + AlCl 3. Such depictions may be simplistic because of ion-pairing between the acetyl cation (an acylium cation) and the ...
Chemical formula. C 9 H 10 O 2: Molar mass: 150.177 g·mol −1 ... Acetanisole can be prepared synthetically by Friedel-Crafts acylation of anisole with acetyl chloride:
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Chloroacetyl chloride is bifunctional—the acyl chloride easily forms esters [4] and amides, while the other end of the molecule is able to form other linkages, e.g. with amines. The use of chloroacetyl chloride in the synthesis of lidocaine is illustrative: [ 5 ]
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