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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, CH3COCl.
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).
Fries rearrangement. The Fries rearrangement, named for the German chemist Karl Theophil Fries, is a rearrangement reaction of a phenolic ester to a hydroxy aryl ketone by catalysis of Lewis acids. [1][2][3][4] It involves migration of an acyl group of phenol ester to the aryl ring. The reaction is ortho and para selective and one of the two ...
Phenolates. Structural formula of the phenolate ion. Phenolates (also called phenoxides) are anions, salts, and esters of phenols, containing the phenolate ion. They may be formed by reaction of phenols with strong base. [1]
The Schotten–Baumann reaction is a method to synthesize amides from amines and acid chlorides: An example of a Schotten-Baumann reaction. Benzylamine reacts with acetyl chloride under Schotten-Baumann conditions to form N -benzylacetamide. Schotten–Baumann reaction also refers to the conversion of acid chloride to esters.
haloform-reaction. RSC ontology ID. RXNO:0000689. In chemistry, the haloform reaction (also referred to as the Lieben haloform reaction) is a chemical reaction in which a haloform (CHX3, where X is a halogen) is produced by the exhaustive halogenation of an acetyl group (R−C (=O)CH3, where R can be either a hydrogen atom, an alkyl or an aryl ...
The reaction proceeds through generation of an acylium center. The reaction is completed by deprotonation of the arenium ion by AlCl 4 −, regenerating the AlCl 3 catalyst. However, in contrast to the truly catalytic alkylation reaction, the formed ketone is a moderate Lewis base, which forms a complex with the strong Lewis acid aluminum ...
The major use of chloroacetyl chloride is as an intermediate in the production of herbicides in the chloroacetanilide family including metolachlor, acetochlor, alachlor and butachlor; an estimated 100 million pounds are used annually. Some chloroacetyl chloride is also used to produce phenacyl chloride, another chemical intermediate, also used ...