Triethyl orthoformate
Encyclopedia
Triethyl orthoformate is an orthoester
of formic acid
. It is commercially available. The industrial synthesis is from hydrogen cyanide and ethanol.
It may also be prepared from the reaction of sodium ethoxide
and chloroform
:
Triethyl orthoformate participates in the Bodroux-Chichibabin aldehyde synthesis
, for example:
Orthoester
In organic chemistry, an orthoester is a functional group containing three alkoxy groups attached to one carbon atom, i.e. with the general formula RC3. The name can also refer to any organic compound that contains this functional group. An example of an orthoester is ethyl orthoacetate, CH3C3,...
of formic acid
Formic acid
Formic acid is the simplest carboxylic acid. Its chemical formula is HCOOH or HCO2H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in the venom of bee and ant stings. In fact, its name comes from the Latin word for ant, formica, referring to its early...
. It is commercially available. The industrial synthesis is from hydrogen cyanide and ethanol.
It may also be prepared from the reaction of sodium ethoxide
Sodium ethoxide
Sodium ethoxide is an alkoxide salt with the chemical formula C2H5ONa.-Preparation:It is commercially available as a white solid, or as a solution in ethanol. It is easily prepared in the laboratory by reacting sodium metal with ethanol:...
and chloroform
Chloroform
Chloroform is an organic compound with formula CHCl3. It is one of the four chloromethanes. The colorless, sweet-smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous...
:
- CHCl3 + 3 Na + 3 EtOH → HC(OEt)3 + 3/2 H2 + 3 NaCl
Triethyl orthoformate participates in the Bodroux-Chichibabin aldehyde synthesis
Bodroux-Chichibabin aldehyde synthesis
The Bodroux-Chichibabin aldehyde synthesis is a chemical reaction whereby a Grignard reagent is converted to an aldehyde one carbon longer.Reaction of a Grignard reagent with triethyl orthoformate gives an acetal, which can be hydrolyzed to an aldehyde. For example, the synthesis of n-hexanal:...
, for example:
