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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, CH 3 COCl. Acyl chlorides are the ...
In addition to aliphatic, aromatic, and α,β-unsaturated aldehydes, acyl nitriles and 1,2-diketones are also suitable substrates. Few methods exist for decarbonylation. One illustrative application is the synthesis of the core nucleus of FR-900482. [3] Note that the ester is unaffected by the rhodium reagent. Synthetic example of Tsuji ...
In the Weinreb ketone synthesis, an acyl chloride is first converted to the Weinreb amide, ... To selectively form the allyl alcohol and avoid the 1,4 product, ...
Oxalyl chloride is mainly used together with a N,N-dimethylformamide catalyst in organic synthesis for the preparation of acyl chlorides from the corresponding carboxylic acids. [ citation needed ] Like thionyl chloride , the reagent degrades into volatile side products in this application, which simplifies workup.
The Weinreb–Nahm ketone synthesis. The major advantage of this method over addition of organometallic reagents to more typical acyl compounds is that it avoids the common problem of over-addition. For these latter reactions, two equivalents of the incoming group add to form an alcohol rather than a ketone or aldehyde. This occurs even if the ...
Friedel–Crafts reactions have been used in the synthesis of several triarylmethane and xanthene dyes. [26] Examples are the synthesis of thymolphthalein (a pH indicator) from two equivalents of thymol and phthalic anhydride: A reaction of phthalic anhydride with resorcinol in the presence of zinc chloride gives the fluorophore fluorescein.
The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol . This reaction was developed by Alexander Williamson in 1850. [ 2 ] Typically it involves the reaction of an alkoxide ion with a primary alkyl halide via an S N 2 reaction .
Substituted ketenes can be prepared from acyl chlorides by an elimination reaction in which HCl is lost: Formation of a ketene from an acyl chloride. In this reaction, a base, usually triethylamine, removes the acidic proton alpha to the carbonyl group, inducing the formation of the carbon-carbon double bond and the loss of a chloride ion: