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Ortho esters are readily hydrolyzed in mild aqueous acid to form esters: . RC(OR ′) 3 + H 2 O → RCO 2 R ′ + 2 R ′ OH. For example, trimethyl orthoformate CH(OCH 3) 3 may be hydrolyzed (under acidic conditions) to methyl formate and methanol; [5] and may be further hydrolyzed (under alkaline conditions) to salts of formic acid and methanol.
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: [1] Bodroux-Chichibabin hexanal [1]
A solution of a carbonyl compound is added to a Grignard reagent. (See gallery) An example of a Grignard reaction (R 2 or R 3 could be hydrogen). The Grignard reaction (French:) is an organometallic chemical reaction in which, according to the classical definition, carbon alkyl, allyl, vinyl, or aryl magnesium halides (Grignard reagent) are added to the carbonyl groups of either an aldehyde or ...
Grignard reagents or Grignard compounds are chemical compounds with the general formula R−Mg−X, where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride Cl−Mg−CH 3 and phenylmagnesium bromide (C 6 H 5)−Mg−Br. They are a subclass of the organomagnesium compounds.
The Bouveault aldehyde synthesis (also known as the Bouveault reaction) is a one-pot substitution reaction that replaces an alkyl or aryl halide with a formyl group using a N,N-disubstituted formamide. [1] [2] For primary alkyl halides this produces the homologous aldehyde one carbon longer. For aryl halides this produces the corresponding ...
The reaction mechanism [8] of the Bartoli indole synthesis is illustrated below using o-nitrotoluene (1) and propenyl Grignard (2) to form 3,7-dimethylindole (13). The mechanism of the Bartoli indole synthesis. The mechanism begins by the addition of the Grignard reagent (2) onto the nitroarene (1) to form intermediate 3.
The Kulinkovich reaction describes the organic synthesis of substituted cyclopropanols through reaction of esters with dialkyldialkoxytitanium reagents, which are generated in situ from Grignard reagents containing a hydrogen in beta-position and titanium(IV) alkoxides such as titanium isopropoxide. [1]
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. [5]