Octet / Reactions
Acetoacetic Ester Synthesis
Acetoacetic Ester Synthesis (Substitution.) Converts CCOC(=O)CC(=O)C to CCC(=O)C using NaOEt, R-X, then H₃O⁺/heat.
Substitution
Reaction details
Name
Acetoacetic Ester Synthesis
Type
Substitution
Starting Material
CCOC(=O)CC(=O)C
Product
CCC(=O)C
Reagents
NaOEt
R-X
then H₃O⁺/heat
Mechanism
- Smiles
CCOC(=O)CC(=O)C
- Description
Ethyl acetoacetate: acidic α-H (pKa ~11)
- Smiles
CCOC(=O)CC(=O)C
- Description
Enolate alkylation
- Smiles
CCC(=O)C
- Description
Hydrolysis and decarboxylation → substituted ketone
Tips
Makes substituted ketones (methyl ketones)
Decarboxylation of β-keto acid
Can alkylate twice
Partner: malonic ester synthesis (makes acids)
Related Reactions
malonic-ester-synthesis
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