Everything about Ethyl Acetoacetate totally explained
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The
organic compound ethyl acetoacetate (
EAA) is the
ethyl ester of
acetoacetic acid. It is a
solvent, and is used as a
chemical intermediate in the production of a wide variety of compounds, such as
amino acids,
analgesics,
antibiotics,
antimalarial agents,
antipyrene and
aminopyrene, and
vitamin B1; and also in the manufacture of
dyes,
inks,
lacquers,
perfumes,
plastics, and
yellow paint pigments. Alone, it's used as a
flavoring for
food.
Preparation
Ethyl acetoacetate may be prepared via the
Claisen condensation of
ethyl acetate. Two moles of ethyl acetate condense to form one mole each of ethyl acetoacetate and ethanol.
Another method is to use acetyl ketene and ethanol. They directly form ethyl acetoacetate, and the yield is good, so this method is widely used in industry, but acetyl ketene is very dangerous.
Chemistry
Ethyl acetoacetate is often used in the
acetoacetic ester synthesis similar to
diethyl malonate in the
Malonic ester synthesis or the
Knoevenagel condensation. The protons alpha to
carbonyl groups are easily deprotonated and then the carbanion formed can undergo
nucleophilic substitution. A subsequent
thermal decarboxylation is also possible.
Analysis
Ethyl acetoacetate is an
ester of a β-
keto carbonic acid and therefore has a strong
Keto-enol tautomerism. The enolate forms purple complexes with iron(III) salts:
Further Information
Get more info on 'Ethyl Acetoacetate'.
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