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Related Concept Videos

Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration02:35

Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

Overview
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more substituted...
Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis02:29

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
Benzene to Phenol via Cumene: Hock Process01:27

Benzene to Phenol via Cumene: Hock Process

The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene hydroperoxide...

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Related Experiment Video

Updated: Jun 26, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

Convenient method for preparing benzyl ethers and esters using 2-benzyloxypyridine.

Susana S Lopez1, Gregory B Dudley

  • 1Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA.

Beilstein Journal of Organic Chemistry
|December 24, 2008
PubMed
Summary

A new reagent, 2-Benzyloxy-1-methylpyridinium triflate, offers a mild and effective method for synthesizing benzyl ethers and esters. The revised protocol generates the active reagent in situ, simplifying the process.

Keywords:
alcoholsalkylationbenzylelectrophilic substitutionestersethersprotecting groupsreagent

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Published on: February 7, 2019

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Benzyl ethers and esters are important functional groups in organic synthesis.
  • Existing methods for benzyl ether and ester synthesis can be harsh or inefficient.

Purpose of the Study:

  • To introduce and optimize a new reagent for benzyl ether and ester synthesis.
  • To develop a convenient and effective in situ protocol for generating the active reagent.
  • To explore the scope of the methodology for synthesizing other arylmethyl ethers.

Main Methods:

  • N-methylation of 2-benzyloxypyridine to generate the active reagent in situ.
  • Optimization of reaction conditions, including solvent choice (toluene vs. trifluorotoluene).
  • Application of the methodology to synthesize various benzyl ethers, esters, and other arylmethyl ethers.

Main Results:

  • 2-Benzyloxy-1-methylpyridinium triflate (1) proved to be a mild and effective reagent.
  • The in situ generation protocol simplifies the synthesis of benzyl ethers and esters.
  • The methodology was successfully extended to the synthesis of other arylmethyl ethers.

Conclusions:

  • The revised benzyl transfer protocol using 2-Benzyloxy-1-methylpyridinium triflate is a valuable addition to synthetic organic chemistry.
  • This method offers a mild, convenient, and effective route for synthesizing benzyl and arylmethyl ethers and esters.