I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
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.
Hazard Statements: H228-H314-H335-H500-X
Flammable solid. Causes severe skin burns and eye damage. May cause respiratory irritation. May form combustible dust concentrations in air
Precautionary Statements: P210-P235+P410-P240-P241-P260-P264b-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep cool. Protect from sunlight. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant