Triethyl orthoformate

Triethyl orthoformate
IUPAC name Diethoxymethoxyethane
Other names Triethoxymethane; Ethyl orthoformate
Identifiers
CAS number	122-51-0 Y
PubChem	31214
Jmol-3D images	Image 1
SMILES CCOC(OCC)OCC
Properties
Molecular formula	C7H16O3
Molar mass	148.2 g mol−1
Density	0.891 g/mL
Melting point	-76 °C, 197 K, -105 °F
Boiling point	146 °C, 419 K, 295 °F
Hazards
MSDS	Fischer Scientific
Y orthoformate (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

• Triethyl orthoacetate
• Trimethyl orthoformate

References

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., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1P0258 ; Coll. Vol. 1: 258 
3. ^ G. Bryant Bachman (1943), "n-Hexaldehyde", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV2P0323 ; Coll. Vol. 2: 323