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Sodium ethoxide is used as a strong base in organic synthesis. It is actively involved in the Claisen condensation, Stobbe reaction and Wolf-kishner reduction. It is an important starting material for the synthesis of ethyl ester and diethyl ester of malonic acid. In Williamson ether synthesis, it reacts with ethyl bromide to form diethyl ether. It is widely used as a base for the generation of carbanions which are utilized for alkylation and condensation reactions.
In reactions where the presence of excess ethanol is undesirable, the use of pre-formed solid sodium ethoxide is much more convenient and safer than preparation in situ from sodium metal. This applies to many literature condensation reactions which employ powdered sodium in, for example ether or toluene, where the difficulty and hazards of obtaining a satisfactory sodium dispersion can be considerable. Solid sodium ethoxide often gives superior results, with better control of exothermic reactions.
Extensively used as a base for the generation of carbanions in a variety of alkylation and condensation reactions. Organic Syntheses examples of the use of solid sodium ethoxide include:
Condensation of acetone with ethyl acetate: Org. Synth. Coll., 3, 17 (1955). Benzoylation of acetophenone with ethyl benzoate: Org. Synth. Coll., 3, 251 (1955). ɑ-Formylations with ethyl formate: Org. Synth. Coll., 3, 300 (1955); 4, 536 (1963). ɑ-Ethoxalylation of diethyl succinate with diethyl oxalate: Org. Synth. Coll., 5, 687 (1973).
Sanchez, B. S.; Benitez, B.; Querini, C. A.; Mendow, G. Transesterification of sunflower oil with ethanol using sodium ethoxide as catalyst. Effect of the reaction conditions. Fuel Process. Technol. 2015, 131, 29-35.
Lyth, S. M.; Shao, H.; Liu, J.; Sasaki, K.; Akiba, E. Hydrogen adsorption on graphene foam synthesized by combustion of sodium ethoxide. Int. J. Hydrogen Energy 2014, 39 (1), 376-380.
Gefahrenhinweise (EU): H251-H314-H318
Self-heating: may catch fire. Causes severe skin burns and eye damage. Causes serious eye damage.
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