Alkyl and Acyl Halides with the Sodio-derivatives of Ethyl Cyanoacetate

Reaction XLIV. (c) Condensation of Alkyl and Acyl Halides with the Sodio-derivatives of Ethyl Cyanoacetate. (B., 20, R., 477 21, R., 353  

)—Cyanoacetic, CH CNICOOCjHj, has similar properties to malonic and acetoacetic esters, inasmuch as the methylene hydrogen atoms are successively replaceable by sodium and this latter by alkyl and acyl radicals. 

The groups C 0 and C N resemble one another in many of their reactions. It may be noted that unsaturated groups always tend to give an acid character to any compound in which they occur. 

Reaction XLV. Condensation of Aldehydes and Ketones with certain Esters under the influence of Acetic Anhydride, Hydrochloric Add, Sodium Ethoxide or certain bases. (A., 218, 172 B., 29, 172 30, 481 31, 735, 2585.)—1 mol. of an aldehyde can be made to condense with 1 mol. of an ester containing an a-methylene group, thus 

If hydrochloric acid or acetic anhydride be used, both aliphatic and aromatic aldehydes can be employed, but if sodium ethoxide or small quantities of diethylamine, piperidine, quinoline, etc., be taken, aromatic aldehydes only will react. In these reactions the methyl gives better results than the ethyl ester. 

---