Bailey, William J. et al. published their research in Journal of the American Chemical Society in 1959 | CAS: 4435-14-7

Pyrolysis of esters. XVIII. Synthesis of nitriles by pyrolysis of cyanoacetic esters was written by Bailey, William J.;Daly, John J. Jr.. And the article was included in Journal of the American Chemical Society in 1959.Recommanded Product: 2-Cyclohexylacetonitrile This article mentions the following:

The pyrolysis of cyanoacetic esters was investigated as a convenient method of synthesis for the corresponding nitriles. NCCH₂CO₂Et (169.5 g.), 118.8 g. EtAc, 11.7 g. NH₄OAc, 18 g. AcOH, 300 cc. 95% EtOH, and 3 g. Pd-C hydrogenated 36 hrs. at room temperature yielded 223.5 g. EtMeCHCH(CN)CO₂Et (I), b₉ 103-4.5鎺? n²⁵_D 1.4268. I (153 g.) added dropwise during 3.75 hrs. to a Vycor tube packed with glass helices at 520鎺?and the resulting pyrolyzate distilled yielded 63.7 g. EtMeCHCH₂CN, b₉₂ 88鎺?n²⁶_D 1.4051. Et cyclohexylidenecyanoacetate (93 g.), b₉ 148-9鎺? n²⁵_D 1.4938, obtained in 83% yield by the condensation of cyclohexanone and NCCH₂CO₂Et, hydrogenated catalytically gave 86 g. Et cyclohexylcyanoacetate (II), b₁₂ 146-8鎺? n²⁵_D 1.4580. II (80 g.) pyrolyzed during 2 hrs. at 520鎺?gave 38.8 g. cyclohexylacetonitrile, b₁₂ 86鎺? n²⁵_D 1.4548. Na (46 g.) in 500 cc. absolute EtOH treated with 226 g. NCCH₂CO₂Et, stirred 15 min., treated rapidly with 254 g. (CH₂CH₂Cl)₂, refluxed 48 hrs., treated with 46 g. Na in 500 cc. absolute EtOH, refluxed 72 hrs., and evaporated, the residue dissolved in H₂O, the solution extracted with Et₂O, and the extract distilled gave 200 g. 1-cyano-1-carbethoxycyclopentane (III), b₁₈ 118鎺? n²⁵_D 1.4452. III (101 g.), pyrolyzed during 2.8 hrs. at 510鎺?in the usual manner and the pyrolyzate fractionated gave 47.3 g. cyclopentanecarbonitrile, b₂₀ 67-8鎺? n²⁵_D 1.4403, and 11 g. unchanged III. Et₂C(CN)CO₂Et (57 g.), b₁₀ 92鎺? n²⁷_D 1.4200, pyrolyzed in the usual manner during 1.7 hrs. at 510鎺?and fractionated gave 20.5 g. Et₂CHCN, b₃₈ 60-2鎺? n²⁶_D 1.3995, and 9.5 g. unchanged starting material. Na (18 g.) in 400 cc. absolute EtOH and 202 g. Br(CH₂)₃Br added simultaneously with stirring to 27.6 g. Na in 600 cc. absolute EtOH and 135.6 g. NCCH₂CO₂Et during 1 hr., heated 1.5 hrs., the EtOH distilled, the residue extracted with H₂O, the extract re姣泋td. with C₆H₆, and the combined extract and original organic layer distilled yielded 110 g. 1-cyano-1-carbethoxycyclobutane (IV), b₁₀ 94.5-7.5鎺? n²⁴_D 1.4395. IV (39.5 g.) pyrolyzed during 1 hr. at 520鎺?and the product fractionated gave 7.5 g. crude CH₂:CHCN, b. 76-7鎺?(BrCH₂CHBrCN m. 131-2鎺?. EtMeC:C(CN)CO₂Et (167 g.), b₉ 111-12鎺? n²⁵_D 1.4648, pyrolyzed during 3.75 hrs. at 510鎺?and the pyrolyzate fractionated gave 62.3 g. mixture of 80-5% EtMeC:CHCN and 15-20% MeCH:CMeCH₂CN, b_80-4 90-1鎺? n²⁵_D 1.4386, and 42 g. starting ester. Et cyclohexylidenecyanoacetate (158 g.) pyrolyzed during 3.2 hrs. at 510鎺?and the product fractionated gave 65.7 g. mixture of 85-90% 1-cyclohexenylacetonitrile and 5-10% cyclohexylideneacetonitrile, b₁₀ 89.5-90鎺? n²⁵_D 1.4832. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Recommanded Product: 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Recommanded Product: 2-Cyclohexylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts