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Oxalyl chloride is an organic chemical compound with the formula Cl−C(=O)−C(=O)−Cl. This colorless, sharp-smelling liquid, the di acyl chloride of oxalic acid , is a useful reagent in organic synthesis .
In organic chemistry, the Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol (−OH) is oxidized to an aldehyde (−CH=O) or ketone (>C=O) using oxalyl chloride, dimethyl sulfoxide (DMSO) and an organic base, such as triethylamine.
Swern oxidation uses oxalyl chloride, dimethylsulfoxide, and an organic base, such as triethylamine. The by-products are dimethyl sulfide (Me 2 S), carbon monoxide (CO), carbon dioxide (CO 2 ) and – when triethylamine is used as base – triethylammonium chloride (C 6 H 15 NHCl).
The Stollé synthesis is a series of chemical reactions that produce oxindoles from anilines and α-haloacid chlorides (or oxalyl chloride). [1] [2] [3] [4]
Peroxyoxalates are esters initially formed by the reaction of hydrogen peroxide with oxalate diesters or oxalyl chloride, with or without base, although the reaction is faster with base: Peroxyoxalates are intermediates that will rapidly transform into 1,2-dioxetanedione, another high-energy intermediate.
Some derivatives of formic acid, like formyl chloride (−COCl), undergo spontaneous decarbonylation at room temperature (or below). Reactions involving oxalyl chloride (COCl) 2 (e.g., hydrolysis, reaction with carboxylic acids, Swern oxidation, etc.) often liberate both carbon dioxide and carbon monoxide via a fragmentation process.
Thionyl chloride is commonly used to generate the acid chloride in situ, care being taken to maintain anhydrous conditions, as oxazolines can be ring-opened by chloride if the imine becomes protonated. [8] The reaction is typically performed at room temperature. If reagents milder than SOCl 2 are required, oxalyl chloride can be used. [9]
MCPO is synthesized by reacting methyl salicylate with oxalyl chloride in a solution of THF and pyridine: [1] Pyridine reacts with HCl produced forming the THF insoluble pyridine hydrochloride salt. Water is then added to the solution to dissolve the precipitated pyridine HCl and decrease the solubility of the MCPO in solution, causing it to ...