Triethyl orthoformate

Triethyl orthoformate is an organic compound with the formula HC(OC2H5)3. It is a colorless volatile liquid. It is orthoester of formic acid. It is commercially available. The industrial synthesis is from hydrogen cyanide and ethanol.[1]

Triethyl orthoformate
Names
IUPAC name
Diethoxymethoxyethane
Other names
Triethoxymethane; Ethyl orthoformate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.138
EC Number
  • 204-550-4
UNII
UN number 2524
Properties
C7H16O3
Molar mass 148.202 g·mol−1
Density 0.891 g/mL
Melting point −76 °C (−105 °F; 197 K)
Boiling point 146 °C (295 °F; 419 K)
Hazards
Safety data sheet Fischer Scientific
GHS pictograms
GHS Signal word Warning
GHS hazard statements
 H226, H315, H319, H335
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+352, P303+361+353, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P370+378, P403+233, P403+235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

It may also be prepared from the reaction of sodium ethoxide and chloroform:[2]

CHCl3 + 3 Na+ + 3 EtO− → HC(OEt)3 + ​3⁄2 H2 + 3 NaCl

Triethyl orthoformate is used in the Bodroux-Chichibabin aldehyde synthesis, for example:[3]

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 complexes to the corresponding ethanol complexes:[4]

[Ni(H2O)6](BF4)2 + 6 HC(OC2H5)3 → [Ni(C2H5OH)6](BF4)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. Ref. J.B.Paine III, J. Org. Chem. 2008, 73, 4929-4938. 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

References
  1. Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 9288
  2. W. E. Kaufmann and E. E. Dreger (1941). "Ethyl orthoformate". Organic Syntheses.; Collective Volume, 1, p. 258
  3. G. Bryant Bachman (1943). "n-Hexaldehyde". Organic Syntheses.; Collective Volume, 2, p. 323
  4. Willem L. Driessen, Jan Reedijk "Solid Solvates: The Use of Weak Ligands in Coordination Chemistry" Inorg. Synth., 1992, Vol. 29,111–118. doi:10.1002/9780470132609.ch27
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