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At large scale, ethyl acetoacetate is industrially produced by treatment of diketene with ethanol. [2] The small scale preparation of ethyl acetoacetate is a classic laboratory procedure. [3] It involves Claisen condensation of ethyl acetate. Two moles of ethyl acetate condense to form one mole each of ethyl acetoacetate and ethanol. [4]
Acetoacetic ester synthesis is a chemical reaction where ethyl acetoacetate is alkylated at the α-carbon to both carbonyl groups and then converted into a ketone, or more specifically an α-substituted acetone. This is very similar to malonic ester synthesis. Acetoacetic ester synthesis equation
Ethyl acetate (systematically ethyl ethanoate, commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula CH 3 CO 2 CH 2 CH 3, simplified to C 4 H 8 O 2.This flammable, colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, and the decaffeination process of tea and coffee.
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 material in organic synthesis, can be prepared using a diketene in reaction with ethanol. They directly form ethyl acetoacetate, and the yield is high when ...
Acetoacetic esters are used for the acetoacetylation reaction, which is widely used in the production of arylide yellows and diarylide dyes. [3] Although the esters can be used in this reaction, diketene also reacts with alcohols and amines to the corresponding acetoacetic acid derivatives in a process called acetoacetylation.
Ethyl and benzyl esters are easily made thereby, and the reaction is noteworthy in that even the highly hindered tert-butyl alcohol gives very high yields in this synthesis. [ 8 ] Levi and Zanetti extended the Knorr synthesis in 1894 to the use of acetylacetone (2,4-pentanedione) in reaction with ethyl 2-oximinoacetoacetate.
The reaction mechanism of the Biginelli reaction is a series of bimolecular reactions leading to the desired dihydropyrimidinone. [14]According to a mechanism proposed by Sweet in 1973 the aldol condensation of ethylacetoacetate 1 and the aryl aldehyde is the rate-limiting step leading to the carbenium ion 2.
The reaction has been demonstrated to proceed in water as reaction solvent and with direct aromatization by ferric chloride, manganese dioxide or potassium permanganate in a one-pot synthesis. [4] Hantzsch reaction with ammonium acetate, ethyl acetoacetate, formaldehyde and ferric chloride