McElvain, S. M.; Clarke, Robert L. published the artcile< Ketene acetals. XVIII. Pentaethoxyethane and tetraethoxyethylene (diethoxyketene diethyl acetal)>, Recommanded Product: 2,2-Diethoxyacetonitrile, the main research area is .
Because Scheibler (C.A. 20, 2824) has reported that tetraethoxyethylene (diethoxyketene di-Et acetal) (I) dissociate spontaneously into C(OEt)2, an unequivocal synthesis of I was desirable. (EtO)2CHCO2Et (II) yields 84% (EtO)2CHCONH2 (III) and this with Et3N gives 76-9% (EtO)2CHCN (IV). By the method of M. and Nelson (C.A. 36, 5772.3) IV yields 66-71% (EtO)2CHC(OEt):NH2Cl (V); addition of 23.3 g. V to 30.6 g. K2CO3 in 40 ml. H2O (covered with 60 ml. ether) at -5° and shaking 1 min. give 80% Et diethoxyacetimidate (VI), b20 91-2°, nD25 1.4147, d425 0.957. VI (47.5 g.) and 104 g. absolute EtOH, kept 4 days at room temperature, give 42% NH4Cl; the remainder of the N was recovered as III; when the alc. solution was distilled, the only products isolated were a small quantity of ether and 26% II; however, if the alc. filtrate was made alk. (to phenolphthalein) with EtONa before heat was applied, there were formed 8% II, 44% III, 8% V, and 12% Et diethoxyorthoacetate (pentaethoxyethane) (VII), b8 85-6°, b. 205-7°, nD25 1.4072, d425 0.935. VII (4.7 g.), added (10 min.) to 0.08 mole EtNa in petr. ether in a N atm., gives 39% I, b5 70-1°, b740 195-6°, nD25 1.4213, d425 0.949; it shows no tendency to dissociate With EtOH I gives VII; with Br it yields (CO2Et)2 and, presumably, EtBr. (CONH2)2 m. 350° (decomposition, Cu block) or decompose 340° in a sealed tube; Michael (Ber. 28, 1632 (1895)) reported a m.p. of 417-19° (decomposition).
Journal of the American Chemical Society published new progress about 6136-93-2. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Recommanded Product: 2,2-Diethoxyacetonitrile.
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts