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Related Concept Videos

Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

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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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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One-Pot Synthesis of Abietane-Type Hydroxamic Acids: Process Optimization and Mechanistic Insights.

William E Mendoza-Hernández1, Ramón J Zaragozá2, Urbano Díaz1

  • 1Instituto de Tecnología Química, Consejo Superior de Investigaciones Científicas-Universitat Politècnica de València, 46022 Valencia, Spain.

Molecules (Basel, Switzerland)
|May 27, 2026
PubMed
Summary

This study presents a new one-pot method for synthesizing hydroxamic acids from challenging abietane-type resin acids using diethyl chlorophosphate (DCP). Optimized isolation techniques significantly improved yields for these valuable natural product derivatives.

Keywords:
abietaneabietic aciddehydroabietic acidhydroxamic acidsynthesis

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Published on: February 7, 2019

Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Medicinal Chemistry

Background:

  • Synthesis of hydroxamic acids from sterically hindered substrates like abietane-type resin acids is synthetically challenging.
  • Abietane-type resin acids are abundant natural products with potential applications.

Purpose of the Study:

  • To develop an efficient one-pot protocol for the direct conversion of abietic and dehydroabietic acids into their hydroxamic derivatives.
  • To identify optimal reagents and conditions for this transformation.
  • To elucidate the reaction mechanism and chemoselectivity.

Main Methods:

  • Systematic screening of activating agents, identifying diethyl chlorophosphate (DCP).
  • Optimization of aqueous work-up to minimize water for improved isolation of polar products.
  • Isolation and characterization of the diethyl phosphate mixed anhydride intermediate.
  • Density Functional Theory (DFT) calculations (M062X/6-31G**) to study the reaction mechanism and transition states.

Main Results:

  • Achieved 65% isolated yield for abietic acid hydroxamic derivative and 74% for dehydroabietic acid derivative.
  • Identified DCP as the optimal reagent for hydroxyamidation.
  • Demonstrated the importance of minimizing water during work-up for product recovery.
  • Provided experimental evidence for the diethyl phosphate mixed anhydride intermediate.
  • DFT calculations revealed a concerted transition state and explained the kinetic preference for N-hydroxy amide formation over the thermodynamic ester product.

Conclusions:

  • Established a practical and scalable one-pot methodology for synthesizing hydroxamic acids from sterically hindered abietane-type resin acids.
  • The combined experimental and theoretical approach provides a deep understanding of the reaction mechanism and chemoselectivity.
  • This method enables the functionalization of abundant natural terpenoids, opening avenues for new applications.