Triethyl orthoformate: Difference between revisions

| Verifiedfields = changed

| verifiedrevid =

|ImageFile=Triethoxymethane.svg

|ImageSize=180px

| ImageAlt = Structural formula

| ImageFile1 = Triethyl-orthoformate-3D-balls.png

| ImageSize1 = 180

| ImageAlt1 = Ball-and-stick model

| PIN=(Diethoxymethoxy)ethane

|OtherNames=Triethoxymethane; Ethyl orthoformate

| CASNo_Ref = {{cascite|correct|CAS}}

| PubChem=31214

| EC_number = 204-550-4

| UNNumber = 2524

| UNII = 355LRR361Q

| ChEMBL = 1476236

| SMILES=CCOC(OCC)OCC

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 28955

| InChI = 1/C7H16O3/c1-4-8-7(9-5-2)10-6-3/h7H,4-6H2,1-3H3

| InChIKey = GKASDNZWUGIAMG-UHFFFAOYAW

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C7H16O3/c1-4-8-7(9-5-2)10-6-3/h7H,4-6H2,1-3H3

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = GKASDNZWUGIAMG-UHFFFAOYSA-N

| C=7 | H=16 | O=3

| Appearance=

| Density=0.891 g/mL

| MeltingPtC= -76

| BoilingPtC= 146

| Solubility=

| GHSPictograms = {{GHS02}}{{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|226|315|319|335}}

| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|280|302+352|303+361+353|304+340|305+351+338|312|321|332+313|337+313|362|370+378|403+233|403+235|405|501}}

| = [https://fscimage.fishersci.com/msds/97204.htm Fischer Scientific]

| FlashPt=

| AutoignitionPt =

'''Triethyl orthoformate''' is an [[]] of [[formic acid]] is commercially available. The industrial synthesis is from hydrogen cyanide and ethanol<ref>Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 9288</ref>

It may also be prepared from the reaction of [[sodium ethoxide]] and [[chloroform]]:<ref>{{OrgSynth | title = Ethyl orthoformate | author = W. E. Kaufmann and E. E. Dreger | prep = CV1P0258 | collvol =1 | collvolpages = 258 | year = 1941}}</ref>

: CHCl₃ + 3 Na + 3 EtOH HC(OEt)₃ + 32 H₂ + 3 NaCl

Triethyl orthoformate in the [[Bodroux-Chichibabin aldehyde synthesis]], for example:<ref>{{OrgSynth | title = ''n''-Hexaldehyde | author = G. Bryant Bachman | collvol = 2 | collvolpages = 323 | year = 1943 | prep = CV2P0323}}</ref>

: 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 complex]]es to the corresponding ethanol complexes:<ref>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}}</ref>

:[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>{{Cite journal|last=Paine|first=John B.|date=July 2008|title=Esters of Pyromellitic Acid. Part I. Esters of Achiral Alcohols: Regioselective Synthesis of Partial and Mixed Pyromellitate Esters, Mechanism of Transesterification in the Quantitative Esterification of the Pyromellitate System Using Orthoformate Esters, and a Facile Synthesis of the Ortho Pyromellitate Diester Substitution Pattern|url=http://dx.doi.org/10.1021/jo800543w|journal=The Journal of Organic Chemistry|volume=73|issue=13|pages=4929–4938|doi=10.1021/jo800543w|pmid=18522420 |issn=0022-3263}}</ref> 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.

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[[Category:Ethyl esters]]