A Low-Cost and Scalable Synthesis of a Cyclohexanone-Related Bifunctional Building Block
Qinghong Zha1, Xiaosheng An1, Ze-Jun Xu1
1State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
ACS Omega
|November 22, 2021
Summary
A new synthetic pathway for 2-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclohexan-1-one was established using affordable reagents and accessible conditions. This practical route achieved a 53% overall yield through a sequence of key chemical transformations.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Developing efficient synthetic routes is crucial for accessing complex organic molecules.
- Cost-effective and scalable methods are highly desirable in chemical synthesis.
Purpose of the Study:
- To establish a practical and efficient synthetic route to 2-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclohexan-1-one.
- To utilize inexpensive starting materials and readily attainable reaction conditions.
Main Methods:
- The synthesis involved a multi-step process including NaOH-mediated aldol condensation.
- Ethylene glycol protection of the ketone, catalytic hydrogenation of the C=C bond and benzene ring using Al-Ni alloy.
- Oxidation of the intermediate cyclohexanol using sodium hypochlorite (NaClO) with TEMPO/KBr.
Main Results:
- The overall transformation yielded 53% of the target compound.
- A single chromatographic purification step was sufficient for isolation.
- The reaction sequence employed cost-effective reagents and manageable conditions.
Conclusions:
- A practical and efficient synthetic strategy for 2-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclohexan-1-one has been successfully developed.
- The described method offers a viable approach for the synthesis of this compound using accessible materials and conditions.
More Related Videos
Related Concept Videos
01:16Cycloaddition Reactions: Overview
2.9K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.9K
![[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2Ffiles%2Fmedia%2Fscience-education%2Fscience-education-thumbs%2F12417.jpg&w=3840&q=75)
01:16[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
10.9K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.9K
01:16Cycloaddition Reactions: MO Requirements for Thermal Activation
3.8K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
3.8K
01:27Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
2.4K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
2.4K
01:28Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation
5.1K
Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
5.1K
02:30Stability of Substituted Cyclohexanes
13.6K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
13.6K