Triethyl orthoformate

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Triethyl orthoformate
Structural formula
Ball-and-stick model
Names
IUPAC name
Diethoxymethoxyethane
Other names
Triethoxymethane; Ethyl orthoformate
Identifiers
122-51-0 YesY
Jmol-3D images Image
PubChem 31214
Properties
C7H16O3
Molar mass 148.20 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
MSDS Fischer Scientific
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/N?)
Infobox references

Triethyl orthoformate is an orthoester of formic acid. It is commercially available. The industrial synthesis is from hydrogen cyanide and ethanol.[1]

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

CHCl3 + 3 Na + 3 EtOH → HC(OEt)3 + 3/2 H2 + 3 NaCl

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

See also[edit]

References[edit]

  1. ^ Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 9288
  2. ^ W. E. Kaufmann and E. E. Dreger (1941). "Ethyl orthoformate". Org. Synth. ; Coll. Vol. 1, p. 258 
  3. ^ a b G. Bryant Bachman (1943). "n-Hexaldehyde". Org. Synth. ; Coll. Vol. 2, p. 323