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Triethyl orthoformate

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Triethyl orthoformate
Identifiers
3D model (JSmol)
ECHA InfoCard 100.004.138 Edit this at Wikidata
  • CCOC(OCC)OCC
Properties
C7H16O3
Molar mass 148.202 g·mol−1
Density 0.891 g/mL
Melting point −76 °C (−105 °F; 197 K)
Boiling point 143 °C (289 °F; 416 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Triethyl orthoformate is an orthoester of formic acid. It is commercially available. It may also be prepared from the reaction of sodium ethoxide and chloroform:[1]

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

Triethyl orthoformate participates in the Bodroux-Chichibabin aldehyde synthesis, for example:[2]

See also

Trimethyl orthoformate [3]

References

  1. ^ W. E. Kaufmann and E. E. Dreger (1941). "Ethyl orthoformate". Organic Syntheses; Collected Volumes, vol. 1, p. 258.
  2. ^ G. Bryant Bachman (1943). "n-Hexaldehyde". Organic Syntheses; Collected Volumes, vol. 2, p. 323.
  3. ^ http://www.sigmaaldrich.com/catalog/ProductDetail.do?N4=108456%7CALDRICH&N5=SEARCH_CONCAT_PNO%7CBRAND_KEY&F=SPEC