Boehme, Horst; Neidlein, Richard published the artcile< The cleavage of orthocarboxylic acid esters with acyl halides and acyl cyanides>, Name: 2,2-Diethoxyacetonitrile, the main research area is .
HC(OPh)3 (I) with acyl halides yields the corresponding carboxylic acid Ph esters and (PhO)2CHCl (II) which reacts readily with PhSH and with Me2NH. Orthocarboxylic acid esters, orthocarbonates, and acetals are cleaved by AcCN with the formation of carboxylic acid esters and derivatives of (EtO)2CHCN (III). I (2.9 g.) and 0.8 g. AcCl kept 5 days at room temperature under N, filtered, and distilled gave 1.1 g. PhOAc, b0.15 40-52°, n20D 1.5012, 1.4 g. II, b0.15 128-30°, and unchanged I, b0.15 175-7°, m. 72-3°. CCl3COCl (1.8 g.) added with cooling under N to 2.9 g. I, kept 2 hrs. at room temperature, and worked up gave 1.9 g. CCl3CO2Ph, b0.2 114-17°, 1.6 g. II, b0.2 128-30°, and 0.8 g. I, b0.2 178-80°, m. 71-2°. II (2.3 g.) in 10 cc. absolute Et2O added dropwise with stirring to 1.1 g. LiAlH4 in 20 cc. Et2O, refluxed briefly, and worked up yielded 1.8 g. (PhO)2CH2, b13 164-5°. II (4.7 g.) in 10 cc. dry Et2O treated with stirring at -50° with 1.8 g. dry Me2NH in a dry stream of N, kept 3 hrs. at -50°, warmed to room temperature, filtered, and distilled gave 0.9 g. (PhO)2CHNMe2, b0·.01 46-8°, and 2.8 g. I. II (2.3 g.) in 30 cc. dry Et2O treated successively with 1.0 g. C5H5N in 8 cc. dry Et2O and 1.1 g. PhSH, refrigerated 30 days, decanted, and worked up yielded 1.3 g. PhSCH(OPh)2, m. 49-50° (Et2O). p-MeOC6H4CH(OEt)2 (10.5 g.) added dropwise at -60° to 6.2 g. AcBr under dry N, warmed to 0°, diluted with 100 cc. absolute petr. ether at room temperature, cooled to -60°, and filtered gave p-MeOC6H4CHBrOEt (IV) which decompose with fuming and elimination of p-MeOC6H4CHO (phenylhydrazone m. 120.5°; semicarbazone m. 208.5°). IV (1.2 g.) and 0.6 g. PhSH in 50 cc. petr. ether treated with cooling with 0.4 g. C5H5N, kept 2 hrs. at room temperature, filtered, washed, and evaporated yielded 0.5 g. p-MeOC6H4CH(SPh)OEt, m. 80-1° (hexane). IV (2.0 g.) in 70 cc. dry petr. ether treated with stirring with 3 cc. 0.01M PhMgBr, refluxed 2 hrs., and worked up gave p-MeOC6H4CH(OEt)Ph, yellowish oil, b0.01 98-100°. AcCN (3.5 g.) added dropwise to 7.4 g. HC(OEt)3, heated 20 hrs. at 80° under N, and distilled gave 0.8 g. HCO2Et, b. 52-7°, n20D 1.3587, 3.6 g. EtOAc, b. 74-5°, n20D 1.3713, and 3.3 g. III, b12 56-8°, n25D 1.3934. PhC(OEt)3 (11.2 g.) and 3.5 g. AcCN heated 50 hrs. at 90° in a sealed tube gave 2.9 g. EtOAc, 0.8 g. AcOC(CN)2Me (V), b15 94-104°, and 4.6 g. (EtO)2C(CN)Ph, b15 126-30°, n20D 1.4815. C(OEt)4 (9.6 g.) and 3.5 g. AcCN heated 48 hrs. at 80-90° gave 3.6 g. EtOAc, some unchanged C(OEt)4, b13 46-8°, n20D 1.3940, and 3.2 g. (EtO)3CCN, b13 58-60°, n20D 1.3995. MeCH(OEt)2 (5.9 g.) and 3.5 g. AcCN heated 16 hrs. at 90° gave 1.4 g. EtOAc, unchanged AcCN, 0.5 g. MeCH(OEt)CN, b10 30-1°, n20D 1.3875, and 1.4 g. V, b11 101-2°, m. 67-8°.
Chemische Berichte published new progress about Esters. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Name: 2,2-Diethoxyacetonitrile.
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts