Triethyl orthoacetate

Triethyl orthoacetate is the organic compound with the formula CH3C(OC2H5)3. It is the ethyl orthoester of acetic acid. It is a colorless oily liquid.

Triethyl orthoacetate
Skeletal formula of Triethylorthoacetate
Skeletal formula of Triethylorthoacetate
Ball-and-stick model of the Triethylorthoacetate molecule
Ball-and-stick model of the Triethylorthoacetate molecule
Names
Preferred IUPAC name
1,1,1-Triethoxyethane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.012
UNII
  • InChI=1S/C8H18O3/c1-5-9-8(4,10-6-2)11-7-3/h5-7H2,1-4H3 ☒N
    Key: NDQXKKFRNOPRDW-UHFFFAOYSA-N ☒N
  • CCOC(C)(OCC)OCC
Properties
C8H18O3
Molar mass 162.229 g·mol−1
Density 0.885 g/mL
Boiling point 142 °C (288 °F; 415 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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Infobox references

Triethyl orthoacetate is used in organic synthesis for acetylation.[1]

It is also used in the Johnson-Claisen rearrangement.[2]

References
  1. B. W. Howk, J. C. Sauer (1959). "Phenylpropargylaldehyde Diethyl Acetal". Organic Syntheses. 39: 59. doi:10.15227/orgsyn.039.0059.
  2. Fernandes, Rodney A.; Chowdhury, Asim K.; Kattanguru, Pullaiah (2014). "The Orthoester Johnson-Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates - Recent Advances". European Journal of Organic Chemistry. 2014 (14): 2833–2871. doi:10.1002/ejoc.201301033.
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