Related Experiment Video
Updated: Jun 1, 2025

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Photoacid-Catalyzed Esterification of Carboxylic Acids Using Eosin Y
Jaya Tripathi1, Harshita Gupta1, Anuj Sharma1
1Department of Chemistry, Indian Institute of Technology, Roorkee, Uttarakhand 247667, India.
A novel photoacid-catalyzed esterification uses eosin Y as a visible-light-activated catalyst. This method efficiently converts carboxylic acids into esters via proton-coupled electron transfer and radical intermediates.
Area of Science:
- Organic Chemistry
- Photocatalysis
- Green Chemistry
Background:
- Esterification is a fundamental organic transformation.
- Traditional methods often require harsh conditions or stoichiometric reagents.
- Developing sustainable catalytic methods is crucial for green chemistry.
Purpose of the Study:
- To introduce a novel photoacid-catalyzed method for esterification.
- To utilize eosin Y as a dual photoacid and photoredox catalyst.
- To achieve efficient ester synthesis under visible light irradiation.
Main Methods:
- Visible light irradiation of carboxylic acids with eosin Y.
- Employing proton-coupled electron transfer (PCET) mechanism.
- Utilizing transient ketyl radical intermediates for coupling with alcohols.
Main Results:
- Eosin Y effectively catalyzed the esterification of various carboxylic acids.
- The reaction proceeded with good to excellent yields of carboxylic esters.
- The mechanism involves PCET and single electron transfer pathways.
Conclusions:
- A new, efficient, and visible-light-driven photoacid-catalyzed esterification has been developed.
- Eosin Y serves as a versatile photocatalyst for this transformation.
- This method offers a sustainable alternative for ester synthesis.
Related Concept Videos
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism
Esters to Carboxylic Acids: Saponification
The reaction requires a base in stoichiometric amounts, which participates in the reaction and is not regenerated later. So, the base acts as a...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

