Tetraethoxymethane
Tetraethoxymethane is a chemical compound which is formally formed by complete ethylation of the hypothetical orthocarbonic acid C4.
History
Tetraethoxymethane was described the first time in 1864.Synthesis
The preparation of tetraethoxymethane from the highly toxic trichloronitromethane is known in the literature and achieves only yields of 46-49 to 58%:The obvious synthetic route from tetrachloromethane does not provide the desired product, as in the homologous tetramethoxymethane.
Starting from the less toxic trichloroacetonitrile, higher yields can be obtained. An alternative reaction, bypassing problematic reactants, is the reaction of dialkyltin dialkoxides with carbon disulfide at elevated temperature in an autoclave:
Another route reacts thallous ethoxide with carbon disulfide in dry methylene dichloride.
A more recent synthesis starts directly from sodium ethoxide, tin(IV)chloride, and carbon disulfide.