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Triethyl orthoformate is an
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The s ...
with the formula HC(OC2H5)3. This colorless volatile liquid, the orthoester of
formic acid Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure . It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Es ...
, is commercially available. The industrial synthesis is from hydrogen cyanide and ethanol. It may also be prepared from the reaction of
sodium ethoxide Sodium ethoxide, also referred to as sodium ethylate, is the ionic, organic compound with the formula , or NaOEt (Et = ethane). It is a white solid, although impure samples appear yellow or brown. It dissolves in polar solvents such as ethanol ...
, formed in-situ from
sodium Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable ...
and absolute
ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...
, and
chloroform Chloroform, or trichloromethane, is an organic compound with formula C H Cl3 and a common organic solvent. It is a colorless, strong-smelling, dense liquid produced on a large scale as a precursor to PTFE. It is also a precursor to various ref ...
: : CHCl3 + 3 Na + 3 EtOH → HC(OEt)3 + H2 + 3 NaCl Triethyl orthoformate is used in the Bodroux-Chichibabin aldehyde synthesis, for example: : RMgBr + HC(OC2H5)3 → RC(H)(OC2H5)2 + MgBr(OC2H5) : RC(H)(OC2H5)2 + H2O → RCHO + 2 C2H5OH In coordination chemistry, it is used to convert
metal aquo complex In chemistry, metal aquo complexes are coordination compounds containing metal ions with only water as a ligand. These complexes are the predominant species in aqueous solutions of many metal salts, such as metal nitrates, sulfates, and perchlorat ...
es to the corresponding ethanol complexes: : i(H2O)6BF4)2 + 6 HC(OC2H5)3i(C2H5OH)6BF4)2 + 6 HC(O)(OC2H5) + 6 HOC2H5 Triethyl orthoformate (TEOF) is an excellent reagent for converting compatible carboxylic acids to ethyl esters. Such carboxylic acids, refluxed neat in excess TEOF until low-boilers cease evolution, are quantitatively converted to the ethyl esters, without need for extraneous catalysis.{{Cite journal, last=Paine, first=John B., date=July 2008, title=Esters of Pyromellitic Acid. Part I. Esters of Achiral Alcohols: Regioselective Synthesis of Partial and Mixed Pyromellitate Esters, Mechanism of Transesterification in the Quantitative Esterification of the Pyromellitate System Using Orthoformate Esters, and a Facile Synthesis of the Ortho Pyromellitate Diester Substitution Pattern, url=http://dx.doi.org/10.1021/jo800543w, journal=The Journal of Organic Chemistry, volume=73, issue=13, pages=4929–4938, doi=10.1021/jo800543w, pmid=18522420 , issn=0022-3263 Alternatively, added to ordinary esterifications using catalytic acid and ethanol, TEOF helps drive esterification to completion by converting the byproduct water formed to ethanol and ethyl formate.


See also

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Trimethyl orthoformate Trimethyl orthoformate (TMOF) is the organic compound with the formula HC(OCH3)3. A colorless liquid, it is the simplest orthoester. It is a reagent used in organic synthesis for the formation of methyl ethers. The product of reaction of an aldeh ...


References

Orthoesters Ethyl esters