Acylation
Alcohol acylation converts acyl chlorides into esters.
- Reagents
- alcohol
- Conditions
- room temperature
- Reaction class
- acylation
- Equation
- R-COCl + R'OH -> R-CO2R' + HCl
Overview
Alcohol acylation converts acyl chlorides into esters.
Transformation
- Equation
- R-COCl + R'OH -> R-CO2R' + HCl
- Reagents
- alcohol
- Environment
- room temperature
- Reaction class
- acylation
- Mechanism
- nucleophilic acyl substitution
- Evidence level
- textbook core
Scope and limitations
- Scope
- Acyl chlorides react rapidly with alcohols to form esters.
- Limitations
- This route records alcoholysis of acyl chlorides; acid chloride reactions release hydrogen chloride.
Related reactions
- Esterification: Carboxylic acids → Esters
Carboxylic acids react with alcohols to form esters.
- Esterification co reactant: Alcohols → Esters
Alcohols combine with carboxylic acids to form esters.
- Hydrolysis: Esters → Carboxylic acids
Hydrolysis converts esters back into carboxylic acid products.
- Hydrolysis co product: Esters → Alcohols
Hydrolysis of an ester also regenerates the alcohol component.
- Chlorination: Carboxylic acids → Acyl chlorides
PCl5 converts carboxylic acids into acyl chlorides.
- Chlorination with thionyl chloride: Carboxylic acids → Acyl chlorides
Thionyl chloride converts carboxylic acids into acyl chlorides with sulfur dioxide and hydrogen chloride as by-products.
- Hydrolysis: Acyl chlorides → Carboxylic acids
Water hydrolyses acyl chlorides to carboxylic acids, releasing hydrogen chloride.
- Acylation: Acyl chlorides → Amides
Ammonia acylation converts acyl chlorides into amides.
- Acylation: Acyl chlorides → N-substituted amides
Amine acylation converts acyl chlorides into N-substituted amides.
- Anhydride alcoholysis: Acid anhydrides → Esters
Alcohol oxygen attacks an anhydride carbonyl and the tetrahedral intermediate expels carboxylate. Proton transfer produces the ester and a carboxylic acid; one acyl fragment transfers to the alcohol.
References
- Organic Chemistry: Chemistry of Acid HalidesJohn McMurry · OpenStax Organic Chemistry · 2023
Supports acid-halide preparation with thionyl chloride and nucleophilic acyl substitution chemistry, including tetrahedral intermediates, hydrolysis, alcoholysis and amine acylation at acid chlorides.