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Related Concept Videos

Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
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Carboxylic Acids to Acid Chlorides01:18

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Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
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Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
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Preparation of Acid Anhydrides01:07

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One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
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Reactions of Acid Anhydrides01:19

Reactions of Acid Anhydrides

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The reactions of acid anhydrides are analogous to the reactions of acid chlorides and proceed via a nucleophilic acyl substitution. They only differ in the identity of the leaving group. During an acid chloride reaction, the leaving group is a chloride ion, and the by-product is hydrochloric acid. However, in an acid anhydride reaction, the leaving group is a carboxylate ion, and the by-product is a carboxylic acid.
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Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

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The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
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Water-compatible acylation reactions with acid chlorides using a flow microreactor.

Hiromichi V Miyagishi1, Daito Takahashi1, Yiyuan Jiang1

  • 1Department of Chemistry, Faculty of Science, Hokkaido University, Kita-10 Nishi-8 Kita-ku, Sapporo 060-0810, Japan. nagaki@sci.hokudai.ac.jp.

Chemical Communications (Cambridge, England)
|March 25, 2026
PubMed
Summary
This summary is machine-generated.

This study introduces a flow microreactor method for efficient acylation reactions in water, achieving high yields and demonstrating practical applications for pharmaceuticals like oseltamivir.

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Area of Science:

  • Organic Chemistry
  • Chemical Engineering
  • Process Chemistry

Background:

  • Acylation reactions are fundamental in organic synthesis.
  • Hydrolysis often limits yields in aqueous acylation reactions.
  • Developing efficient and scalable acylation methods in aqueous media is crucial.

Purpose of the Study:

  • To develop a flow microreactor system for acylation reactions in homogeneous aqueous media.
  • To suppress hydrolysis and enhance reaction yields.
  • To demonstrate the broad applicability and scalability of the developed method.

Main Methods:

  • Utilized a flow microreactor for acylation reactions with acid chlorides.
  • Employed homogeneous aqueous reaction conditions.
  • Performed quenched-flow analysis to study the reaction mechanism.

Main Results:

  • Achieved up to 98% yield in acylation reactions.
  • Identified an associative transition state via quenched-flow analysis.
  • Demonstrated applicability to amines, phenols, thiols, and pharmaceutical compounds.
  • Showcased scalability with oseltamivir acylation at 2.1 g/h throughput.

Conclusions:

  • The flow microreactor system enables highly efficient acylation in aqueous media.
  • The method overcomes hydrolysis limitations, offering high yields and broad substrate scope.
  • The process is scalable and practical for pharmaceutical synthesis.