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Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH 3 CO) 2 O. Commonly abbreviated Ac 2 O , it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis .
Hippuric acid, the benzamide derivative of glycine, cyclizes in the presence of acetic anhydride, condensing to give 2-phenyl-oxazolone. [3] This intermediate also has two acidic protons and reacts with benzaldehyde, acetic anhydride and sodium acetate to a so-called azlactone. This compound on reduction gives access to phenylalanine. [4]
The Boekelheide reaction is a rearrangement of α-picoline-N-oxides to hydroxymethylpyridines. It is named after Virgil Boekelheide who first reported it in 1954. [ 1 ] Originally the reaction was carried out using acetic anhydride , which typically required a period at reflux (~140 °C).
Aside from acetic anhydride, trifluoroacetic anhydride and trifluoromethanesulfonic anhydride have been employed as activators. [4] Common nucleophiles besides acetates are arenes, alkenes, amides, and phenols. The usage of α-acyl sulfoxides and Lewis acids, such as TiCl 4 and SnCl 4, allow the reaction to proceed at lower temperatures (0 °C ...
This hydrolysis is the most heavily exploited reaction for acyl halides as it occurs in the industrial synthesis of acetic acid. an alcohol to form an ester; an amine to form an amide; an aromatic compound, using a Lewis acid catalyst such as AlCl 3, to form an aromatic ketone. [7] See Friedel-Crafts acylation.
TFA is prepared industrially by the electrofluorination of acetyl chloride or acetic anhydride, followed by hydrolysis of the resulting trifluoroacetyl fluoride: [4] CH 3 COCl + 4 HF → CF 3 COF + 3 H 2 + HCl CF 3 COF + H 2 O → CF 3 COOH + HF. Where desired, this compound may be dried by addition of trifluoroacetic anhydride. [5]
As examples, a water molecule easily adds to ketene to give 1,1-dihydroxyethene and acetic anhydride is produced by the reaction of acetic acid with ketene. Reactions between diols (HO−R−OH) and bis-ketenes (O=C=CH−R'−CH=C=O) yield polyesters with a repeat unit of (−O−R−O−CO−R'−CO). Ethyl acetoacetate, an important starting ...
Thioacetic acid is prepared by the reaction of acetic anhydride with hydrogen sulfide: [5] (CH 3 C(O)) 2 O + H 2 S → CH 3 C(O)SH + CH 3 C(O)OH. It has also been produced by the action of phosphorus pentasulfide on glacial acetic acid, followed by distillation.