Scalable Green Approach Toward Fragrant Acetates

Area of Science:

• Green Chemistry
• Biocatalysis
• Organic Synthesis

Background:

• Ethylene glycol diacetate (EGDA) presents advantageous properties for green applications.
• EGDA is a potential substitute for glycerol triacetate (GTA).

Purpose of the Study:

• To investigate lipase-mediated acetylation of diverse alcohols using EGDA as a green solvent.
• To explore the reactivity and selectivity of this enzymatic system for synthesizing fragrant acetates and performing selective transformations.

Main Methods:

• Lipase-mediated acetylation reactions in neat EGDA.
• Synthesis of fragrant acetates from various alcohols.
• Chemo-selective acetylation of (hydroxyalkyl) phenols.
• Kinetic resolution of chiral secondary alcohols.
• Competitive experiments with isomeric alcohol mixtures.

Main Results:

• The enzymatic system demonstrated high reactivity and selectivity towards activated and non-activated alcohols.
• Scalable multigram synthesis of (Z)-hex-3-en-1-yl acetate achieved in 70% yield.
• Successful chemo-selective acetylation of (hydroxyalkyl) phenols.
• Effective kinetic resolution of chiral secondary alcohols.
• Practical synthesis of 1-pentyl acetate in 68% yield from an isomeric alcohol mixture.

Conclusions:

• EGDA is a viable green solvent for lipase-catalyzed acetylation.
• The enzymatic system offers broad applicability for synthesizing fragrant acetates and performing selective transformations.
• This approach enables efficient and selective synthesis of valuable compounds.