Sodium ethoxide

Sodium ethoxide is a chemical compound. It has the chemical formula C₂H₅ONa, sometimes shortened to NaOEt. It is the alkoxide of sodium and ethanol. It is used as a source of the ethoxide anion, C₂H₅O⁻, a strong base that is used to make many different chemicals.

Preparation

Sodium ethoxide is made in a chemical reaction between sodium metal and anhydrous (water-free) ethanol.^[1]

Uses

Sodium ethoxide's chemistry is similar to other alkoxides. It is used in many different types of reaction in organic synthesis, normally as either a base or nucleophile.^[2] Sodium ethoxide and sodium methoxide are some of the most commonly used alkoxides.^[3]

Sources

↑ Evelyn M. Hancock and Arthur C. Cope (1945). "Ethyl (1-ethylpropenyl)methylcyanoacetate". Organic Syntheses. 25: 44. doi:10.15227/orgsyn.025.0044.
↑ Whitaker, K. Sinclair; Whitaker, D. Todd (2001). "Sodium Ethoxide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rs070. ISBN 0-471-93623-5.
↑ Wethman, Robert; Derosa, Joseph; Tran, Van T.; Kang, Taeho; Apolinar, Omar; Abraham, Anuji; Kleinmans, Roman; Wisniewski, Steven R.; Coombs, John R.; Engle, Keary M. (2021). "An Under-Appreciated Source of Reproducibility Issues in Cross-Coupling: Solid-State Decomposition of Primary Sodium Alkoxides in Air". ACS Catalysis. 11 (2): 502–508. doi:10.1021/acscatal.0c04124.

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[1] Evelyn M. Hancock and Arthur C. Cope (1945). "Ethyl (1-ethylpropenyl)methylcyanoacetate". Organic Syntheses. 25: 44. doi:10.15227/orgsyn.025.0044.

[2] Whitaker, K. Sinclair; Whitaker, D. Todd (2001). "Sodium Ethoxide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rs070. ISBN 0-471-93623-5.

[3] Wethman, Robert; Derosa, Joseph; Tran, Van T.; Kang, Taeho; Apolinar, Omar; Abraham, Anuji; Kleinmans, Roman; Wisniewski, Steven R.; Coombs, John R.; Engle, Keary M. (2021). "An Under-Appreciated Source of Reproducibility Issues in Cross-Coupling: Solid-State Decomposition of Primary Sodium Alkoxides in Air". ACS Catalysis. 11 (2): 502–508. doi:10.1021/acscatal.0c04124.

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