Synthesis of Acetoacetic esters

Ethyl acetoacetate ( acetoacetic ester) is used in the synthesis of carboxylic acids, ketones, and heterocyclic compounds.

Synthesis of alkyl acetic acids :-

This involves in the reaction of sodium ethyl acetoacetate with an alkyl halide (RX) followed by acid hydrolysis 

 

The R in alkyl acetic acid comes from the alkyl halide.

Synthesis of dialkyl acetic acid :-

Alkylation of sodium ethyl acetoacetate is first done with RX and then with R'X followed by acid hydrolysis.

Then R and R' in dialkyl acetic acid comes from the alkyl halides.

Synthesis of succinic acids :-

The reaction of sodium ethyl acetoacetate with ethyl chloro acetate (ClCH₂COOC₂H₅) followed by acid hydrolysis gives succinic acid.

 

  If we start with sodium alkyl acetoacetic esters, alkyl succinic acids are formed.

Synthesis of higher normal diacids :-

The reaction of sodium ethyl acetoacetate (2 Molecules) with an alkylene iodide followed by acid hydrolysis gives a normal dicarboxylic acid.

 

Synthesis of α, β Unsaturated acids :-

This involves base catalysed reaction of ethyl acetoacetate with an aldehyde or a ketone followed by acid hydrolysis.

Synthesis of methyl ketones :-

This involves the reaction of sodium ethyl acetoacetate with an alkyl halide (RX) followed by ketonic hydrolysis.

Synthesis of 1, 3 Diketones :-

This involves the reaction of sodium ethyl acetoacetate with acid halides followed by ketonic hydrolysis.

Synthesis of acetonyl acetone :-

This involves the reaction of sodium ethyl acetoacetate with iodine followed by ketonic hydrolysis.

 Synthesis of 4-Methyl uracil :-

Ethyl acetoacetate (in it's enol form) reacts with urea in the presence of phosphoryl chloride to give 4-Methyl uracil. 

Synthesis of antipyrine :-

Ethyl acetoacetate reacts with phenylhydrazine to give antipyrine.

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