Nitriles from esters

The synthesis of ortho esters from nitriles is usually a two-step process involving first the formation of the imino ester hydrochloride and subsequent reaction with an alcohol. Several examples are described in Table I, even a glycol such as ethylene glycol can be used to obtain heterocyclic ortho esters, as shown in Eq. (11). 

Lee, Y. B., Goo, Y. M., Lee, Y. Y. Another evidence for the formation of 2-amino-1,3-oxathiolane tetrahedral intermediate in the Pinner type reaction of nitriles with 2-mercaptoethanol formation of 2-chlorothio esters and 2-mercaptoethyl esters from nitriles. Bull. Korean Chem. 

Synthesis of imino ethers, amidines and orto esters from nitriles (see 1st edition)... 

Carboxylic acid esters from nitriles CN COOR... 

Carboxylic acid co-hydroxyalkyl esters from nitriles and diols... 

Another feature of the McReynolds constants is guidance in the selection of a column that will separate compounds with different functional groups, such as ketones from alcohols, ethers from olefins, and esters from nitriles. If an analyst wishes a column to elute an ester after an alcohol, the stationary phase should have a larger Z value with respect to its Y value. In the same fashion, a stationary should exhibit a larger Y value with respect to Z if an ether is to elute before an alcohol. The appendixes in Reference 12 list McReynolds constants in order of increasing A/ for each probe in successive tables that are handy and greatly facilitate the column selection process. 

Another feature of the McReynolds constants is guidance in the selection of a column that will separate compounds with different functional groups, such as ketones from alcohols, ethers from olefins, esters from nitriles, and so on. If an analyst needs a column to elute an ester after an alcohol, the stationary phase... 

Thiolic acid esters from nitriles via thioiminoester hydrochlorides oc-Hydroxythiolic acid esters from cyanohydrins... 

Carboxylic acids may also be prepared by conversion of nitriles into esters or amides, followed by hydrolysis. See section 118 (Esters from Nitriles) and section 88 ( Amides from Nitriles)... 

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