Ethyl potassium glutarate

Suberic acid from ethyl-potassium glutarate. 

Ethyl cyanoacetate condenses with ketones and ammonia in absolute ethanol at 0-5° to give 44-73% yields of cyclic dicyanoimides. Endocyclic ketones may be used, giving imides in which the two radicals are p>art of an alicyclic ring. The imides are hydrolyzed and decarboxylated in almost theoretical yields to yS,/S-disubstituted glutaric acids. A similar reaction takes place between aldehydes or ketones and cyanoacetamide, NCCHjCONHj, in the presence of piperidine or potassium hydroxide. When aldehydes are used, the condensation products are dicyanoamides, RCH[CH(CN)CONHj]j, rather than cyclic imides. 

Materials. Terephthaldicarboxaldehyde (Aldrich), diethyl bis(hydroxymethyl) malonate (Aldrich), p-toluenesulfonic acid (Aldrich), potassium hydroxide (85 wt%, Fisher), pyridine (Fisher), glutaric dialdehyde (50wt% aqueous solution, Aldrich), ethylene glycol divinyl ether (Aldrich), ethyl glycolate (Aldrich), isophthalic dicarboxaldehyde (Lancaster), propionaldehyde (Eastman Chemical), isovaleraldehyde (Aldrich), 2-ethyl-2-oxazoline (Acros), ammonia (7M in methanol, Acros), l-methoxy-4-(methylthio)benzene (Aldrich), silver... 

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