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Related Concept Videos

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview01:20

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview

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The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids and alcohols in an acidic medium to give esters and water.
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Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

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Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
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Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

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Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
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...
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Esters to Carboxylic Acids: Saponification01:25

Esters to Carboxylic Acids: Saponification

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Esters can be hydrolyzed to carboxylic acids under acidic or basic conditions. Base-promoted hydrolysis of esters is a nucleophilic acyl substitution reaction in which esters react with an aqueous base, followed by an acid to give carboxylic acids. This reaction is also known as saponification because it forms the basis for making soaps from fats.
The reaction requires a base in stoichiometric amounts, which participates in the reaction and is not regenerated later. So, the base acts as a...
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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

β-Dicarbonyl Compounds via Crossed Claisen Condensations

3.3K
Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds.  The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
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Mechanically induced solvent-free esterification method at room temperature.

Lei Zheng1, Chen Sun1, Wenhao Xu1,2

  • 1Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology Hangzhou 310014 P. R. China pharmlab@zjut.edu.cn.

RSC Advances
|April 15, 2022
PubMed
Summary
This summary is machine-generated.

Two new methods use high-speed ball-milling to efficiently synthesize esters at room temperature. These green chemistry approaches offer high yields for esterification and natural product modification.

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Area of Science:

  • Organic Chemistry
  • Green Chemistry
  • Mechanochemistry

Background:

  • Ester synthesis is crucial in organic chemistry.
  • Traditional esterification methods often require harsh conditions or prolonged reaction times.
  • Developing sustainable and efficient synthetic protocols is an ongoing challenge.

Purpose of the Study:

  • To introduce two novel, environmentally friendly methods for ester synthesis.
  • To explore the application of high-speed ball-milling (HSBM) for esterification reactions.
  • To demonstrate the versatility of these methods in natural product synthesis.

Main Methods:

  • High-speed ball-milling (HSBM) at room temperature.
  • Esterification using iodine (I2) and potassium dihydrogen phosphate (KH2PO2).
  • Esterification using potassium iodide (KI) and triethyl phosphite (P(OEt)3).

Main Results:

  • The I2/KH2PO2 protocol yielded esters in 45%–91% within 20 minutes.
  • The KI/P(OEt)3 protocol yielded esters in 24%–85% within 60 minutes.
  • The I2/KH2PO2 method was successfully applied to late-stage diversification of natural products.

Conclusions:

  • HSBM offers a rapid and efficient route for ester synthesis.
  • The developed protocols represent sustainable alternatives to conventional esterification.
  • The I2/KH2PO2 method shows significant potential for complex molecule synthesis and modification.