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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.
Well-known acyl compounds are the acyl chlorides, such as acetyl chloride (CH 3 COCl) and benzoyl chloride (C 6 H 5 COCl). These compounds, which are treated as sources of acylium cations, are good reagents for attaching acyl groups to various substrates.
Trichloroacetyl chloride is the acyl chloride of trichloroacetic acid. It can be formed by reacting chlorine with acetyl chloride or acetaldehyde in the presence of activated charcoal, or by the isomerisation of tetrachloroethylene oxide via heating. It is used in the manufacture of pharmaceuticals and plant protection compounds. [4]
In organic chemistry, an acetyl group is a functional group denoted by the chemical formula −COCH 3 and the structure −C(=O)−CH 3. It is sometimes represented by the symbol Ac [5] [6] (not to be confused with the element actinium). In IUPAC nomenclature, an acetyl group is called an ethanoyl group.
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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Acetyl chloride. This reagent is also common in the laboratory, but its use cogenerates hydrogen chloride, which can be undesirable. [8] Ketene. At one time acetic anhydride was prepared by the reaction of ketene with acetic acid: [11] H 2 C=C=O + CH 3 CO 2 H → (CH 3 CO) 2 O =