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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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Small-Scale Procedure for Acid-Catalyzed Ketal Formation.

Austin C Wright¹, Yun Emily Du¹, Brian M Stoltz¹

¹The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering , California Institute of Technology , MC 101-20 , Pasadena , California 91125 , United States.

The Journal of Organic Chemistry

|August 13, 2019

Summary

A new dehydrative ketalization method offers an alternative to the Dean-Stark protocol. This modified procedure is effective on small scales, complementing existing techniques for chemical synthesis.

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

The Dean-Stark apparatus is a standard method for dehydrative ketalizations.
Limitations exist for small-scale reactions using the traditional Dean-Stark protocol.

Purpose of the Study:

To present a modified procedure for dehydrative ketal protection.
To offer an alternative to the classic Dean-Stark protocol for specific applications.

Main Methods:

A novel apparatus and procedure for dehydrative ketalization were developed.
The method facilitates the removal of water during ketal formation.

Main Results:

The modified procedure demonstrates superior performance compared to the Dean-Stark apparatus on small scales.
This technique serves as a viable complementary approach for dehydrative ketalizations.

Conclusions:

A detailed procedure for the new apparatus is provided.
The modified method enhances efficiency for small-scale dehydrative ketalizations in organic synthesis.