Ethyl Acetoacetate

Ethyl acetoacetate is an organic compound that is the ethyl ester of acetoacetate. The chemical formula of this compound is C₆H₁₀O₃ or CH₃COOCH₂COOC₂H₅. This compound is present as a colourless liquid with a fruity fragrance that is used as a food flavouring. It is also used as a chemical intermediate for the production of various types of chemical compounds. This compound is also used industrially in the production of synthetic dyes and drugs.

Ethyl acetoacetate is industry produced compound. The ethyl acetoacetate structure is produced using the treatment of ethanol with diketene. The production of this compound in the laboratory is a very well-known procedure. This is done by using the process of Claisen condensation of ethyl acetate. 

The reaction produces one molecule of ethyl acetoacetate and one molecule of ethanol from the condensation of two molecules of ethyl acetate. 

CH₃COOCH₂COOC₂H₅ is a primary part of acetoacetate ester synthesis. Now that you have a brief understanding of this compound and its production. Let’s now learn about acetoacetate ester synthesis.

What is Acetoacetate Ester Synthesis?

Ester synthesis of acetoacetate is a chemical reaction where α-substituted acetone and a ketone are produced by the alkylation of ethyl acetoacetate at the α-carbon to the two types of carbonyl groups. 

This chemical reaction uses a strong base that helps deprotonate the dicarbonyl α-carbon. Due to resonance stabilization and enolate conjugation, the dicarbonyl α-carbon is selected over the methyl carbon. The process of preference of one carbon over the other is known as a nucleophilic substitution in this reaction. 

When the ester is heated with aqueous acids, it creates a new hydrolyzed β-keto acid from the alkylated ester. The β-keto acid can then be decarboxylated to form methyl ketone.

That is a brief understanding of ester synthesis, which talked about how the synthesis is completed. Each of these compounds is created by their internal molecular and chemical structure; the ethyl acetoacetate structure or the ethyl acetoacetate formula is C₆H₁₀O₃ or CH₃COOCH₂COOC₂H₅. The chemical and molecular acetoacetate structure is C₄H₅O^3-. The acetoacetate structure is derived from the ester synthesis of compounds such as ethyl acetoacetate.

Some Facts About Ethyl Acetoacetate to Better Understand the Compound

These are some of the important facts about the compound that will help you understand how it works with other compounds and its physical and chemical properties.

Ethyl Acetoacetate Reactions: This compound primarily reacts or is more easily introduced in condensation reactions. Reactions that use Claisen condensation widely use this compound as it is a classic laboratory experiment. This compound is generally used for synthesizing furans, pyrroles, pyridines, pyrazoles, purines, and quinolines.

Ethyl Acetoacetate Density: The ethyl acetoacetate density is 1.02 g/cm³. This means the ethyl acetoacetate density is 1.02 grams per cubic centimeter; in comparison, the density of fresh water is 1 gram per cubic centimeter at four degrees centigrade.

Ethyl Acetoacetate MSDS: MSDS stands for Material Safety Data Sheet. The ethyl acetoacetate MSDS states that this compound is combustible in both liquid and vapour forms with a flashpoint (the lowest temperature at which a combustible material can ignite if provided a source for ignition) of 70 degrees centigrade. This compound is also harmful to the respiratory organs of human beings along with their eyes and skin. Acetoacetate causes skin and eye irritation upon exposure. If this compound is ingested, it can cause gastrointestinal problems with vomiting and diarrhoea. In case of inhalation, this compound can lead to respiratory tract irritation with immediate effects such as drowsiness and dizziness. Repeated and prolonged exposure to this compound can lead to the skin being affected by dermatitis.

If you are exposed to ethyl acetoacetate, these are the safety precautions you will need to follow. In case you are caused eye irritation by exposure to this compound, you need to wash your eyes with cold running water for 15 minutes minimum to get rid of the irritation. If the irritation persists, you need medical assistance. 

If exposure to this compound causes skin irritation, you need to clean the irritation area with cold water. Following that, removing all clothing items that you were wearing during the exposure to acetoacetate needs to be done. Medical aid is necessary if the skin irritation persists or increases. 

In case of ingestion of ethyl acetoacetate, do not induce vomiting and get medical help as quickly as possible. 

If you are exposed to this compound through inhalation, you need immediate medical help, but first, safely removing yourself or others from the area of exposure is needed. Oxygen supply might be needed if the person is not able to breathe or is having trouble breathing.

Ethyl Acetoacetate Molar Mass: The ethyl acetoacetate molecular weight is 130.14 g/mol; in comparison, the molar mass of acetoacetic acid is 102.88 g/mol.

Ethyl Acetoacetate Boiling Point: The boiling point of ethyl acetoacetate is 180.8OC. The melting point of this compound is -45⁰C.

Ethyl Acetoacetate IUPAC Name: The IUPAC name of ethyl acetoacetate is ethyl 3-oxobutanoate.

Solved Examples

Q1: What is the Fragrance of Ethyl Acetoacetate?

A) Fruity

B) Pungent

C) Rotten

D) Sweet

Answer: A) Fruity

Q2: What is the IUPAC Name of Ethyl Acetoacetate?

A) 3Ethyl Acetoacetate

B) 4-Oxobutane ethyl

C) ethyl 3-oxobutanoate

D) Butaneoxyethanoate

Answer: C) ethyl 3-oxobutanoate