Adipic Acid Dimethyl Ester

Definition

Adipic acid dimethyl ester is an organic compound with the chemical formula CH3OOC(CH2)4COOCH3. It is a diester formed from the reaction of adipic acid and methanol. This compound is particularly relevant in the context of intramolecular Claisen condensations and the Dieckmann cyclization, as it can undergo these types of reactions to form cyclic structures.

5 Must Know Facts For Your Next Test

1. Adipic acid dimethyl ester can undergo an intramolecular Claisen condensation to form a cyclic β-keto ester in a Dieckmann cyclization reaction.
2. The Dieckmann cyclization of adipic acid dimethyl ester produces a five-membered ring, which can be further functionalized or transformed into other useful compounds.
3. The methyl ester groups in adipic acid dimethyl ester provide a convenient handle for the Dieckmann cyclization, as they can participate in the intramolecular condensation reaction.
4. The cyclic product formed from the Dieckmann cyclization of adipic acid dimethyl ester is a useful intermediate in the synthesis of various heterocyclic compounds and natural products.
5. Adipic acid dimethyl ester is a versatile building block in organic synthesis, as it can undergo a variety of reactions beyond the Dieckmann cyclization, such as hydrolysis, reduction, and further functionalization.

Review Questions

• Explain the role of adipic acid dimethyl ester in the Dieckmann cyclization reaction.
  • Adipic acid dimethyl ester is a key substrate for the Dieckmann cyclization, a type of intramolecular Claisen condensation. In this reaction, the methyl ester groups of the adipic acid dimethyl ester participate in an intramolecular nucleophilic attack on the carbonyl carbon, forming a cyclic β-keto ester product. The resulting five-membered ring can be further functionalized or used as a versatile intermediate in the synthesis of various heterocyclic compounds and natural products.
• Describe how the structure of adipic acid dimethyl ester enables the Dieckmann cyclization to occur.
  • The structure of adipic acid dimethyl ester, with its two methyl ester groups separated by a four-carbon alkyl chain, is well-suited for the Dieckmann cyclization. The methyl ester groups can act as nucleophiles, attacking the carbonyl carbon of the other ester group in an intramolecular fashion. This intramolecular nature of the reaction is facilitated by the flexible alkyl chain, which allows the reactive groups to come into close proximity and undergo the cyclization to form a five-membered ring.
• Analyze the potential synthetic applications of the cyclic product obtained from the Dieckmann cyclization of adipic acid dimethyl ester.
  • The cyclic β-keto ester product obtained from the Dieckmann cyclization of adipic acid dimethyl ester is a versatile intermediate in organic synthesis. The five-membered ring can be further functionalized through various reactions, such as reduction, hydrolysis, or additional condensation reactions, to access a wide range of heterocyclic compounds and natural product scaffolds. The cyclic structure also provides a useful platform for the construction of more complex molecular architectures, making the Dieckmann cyclization of adipic acid dimethyl ester a valuable synthetic transformation in the field of organic chemistry.

Related terms

Adipic Acid:

Adipic acid is a dicarboxylic acid with the formula (CH2)4(COOH)2. It is a common building block in the synthesis of various polymers, including nylon.

Claisen Condensation:

The Claisen condensation is a carbon-carbon bond-forming reaction between the α-carbon of an ester and the carbonyl carbon of another ester, leading to the formation of a β-keto ester.

Dieckmann Cyclization:

The Dieckmann cyclization is a type of intramolecular Claisen condensation that results in the formation of a cyclic β-keto ester.