Search results
Results from the WOW.Com Content Network
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).
This page was last edited on 28 October 2023, at 00:03 (UTC).; Text is available under the Creative Commons Attribution-ShareAlike 4.0 License; additional terms may apply.
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.
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 ]
Acetyl halide, such as acetyl chloride in the presence of a base like triethylamine [2] Activated ester form of acetic acid, such as a N-hydroxysuccinimide ester, although this is not advisable due to higher costs and difficulties. [3] Acetic anhydride in the presence of base with a catalyst such as pyridine with a bit of DMAP added. [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.
acylation of a benzylamine with acetyl chloride (acetic anhydride is an alternative) In the Fischer peptide synthesis (Emil Fischer, 1903), [6] an α-chloro acid chloride is condensed with the ester of an amino acid. The ester is then hydrolyzed and the acid converted to the acid chloride, enabling the extension of the peptide chain by