Synthetic Uses of Ethyl Acetoacetate

Ethylacetoacetate is capable of reacting with a number of reagents to yield a variety of useful compounds which can not prepared by the regular or normal methods. Saturated monocarboxylic acids, unsaturated acids, dicarboxylic acids, keto acids, ketones, diketones, alicyclic compounds and heterocyclic compounds can be synthesised by the use of ethyl acetoacetate.

Acidic Hydrolysis

Alkyl derivatives of ethylacetoacetate when boiled with concentrated KOH solution followed by acidic hydrolysis yield alkyl acetic acid.

Ketonic Hydrolysis

Alkyl derivatives of ethylacetoacetate when boiled with dilute KOH solution followed by acidic hydrolysis yield alkyl acetic acid.

Synthesis of Ketones

Synthesis of Butanone

Alkylated ethylacetoacetate on ketonic hydrolysis yields higher ketones. Butanone may be synthesized by the following steps-

Synthesis of 1,4-diketone

Synthesis of Acetonyl acetone (Hexane-2,5-dione)

Two moles of sodium salt of Ethyl acetoacetate is treated with iodine followed by ketonic hydrolysis yield 1,4-diketone. Acetonyl acetone or hexane-2,5-dione may be synthesized by the following steps-

Synthesis of Alkyl Acetic Acid

Synthesis of Butanoic Acid

Sodium salt of ethylacetoacetate on with alkyl halide followed by acid hydrolysis yields alkyl acetic acid. Butanoic acid may be synthesized by the following steps-

Synthesis of Dicarboxylic Acid

Synthesis of Adipic Acid

Sodium salt of ethylacetoacetate treated with appropriate bromo ester followed by acid hydrolysis yields dicarboxylic acid. Adipic acid may be synthesized by the following steps-

Synthesis of α,β-Unsaturated Acid

Synthesis of Crotonic Acid

Ethyl acetoacetate undergo knoevenagel condensation with aldehydes in the presence of a base to produce alkyl derivatives which upon acid hydrolysis yield α,β-unsaturated acid. Crotonic acid may be synthesized by the following steps-

Synthesis of Alicyclic Compound

Synthesis of Acetylcyclohexane

Alicyclic compound o ring size 5 to 7 carbons can be synthesized by the reaction of ethylacetoacetate with dihalogen compounds. Acetylcyclohexane may be synthesized by the following steps-

Synthesis of Heterocyclic Compound

Synthesis of 4-Methyl Uracil

Acetylcyclohexane may be synthesized by the treatment of ethylacetoacetate with urea in the presence of POCl₃.

Synthesis of Methyl Isooxazolone

Isooxazolone may be synthesized by the treatment of ethylacetoacetate with hydroxyl amine to form the oxime which being unstable and splits into isooxazolone and ethanol.

Synthesis of Levulinic Acid

Levulinic Acid may be synthesized from ethylacetoacetate by the following steps-

Synthetic Uses of Ethyl Acetoacetate

Synthetic Uses of Ethyl Acetoacetate