Contribution to Our Knowledge of the Terpenes and the Ethereal Oils. Eighty-fourth Paper. Carboxylic Acids of Cyclic Hydrocarbons and Their Transformation Products was written by Wallach, O.. And the article was included in Justus Liebigs Annalen der Chemie in 1907.Name: 2-Cyclohexylacetonitrile This article mentions the following:
Acids and bases containing the characteristic groups in the side chain were studied. 1. Cyclohexanone derivatives. Two isomeric acids, (I) and (II) were formed on dehydrating cyclohexanolacetic acid. Δ2.7-Cyclohexeneacetic acid (II), m. 91°, was prepared as already described (Ibid., 347, 329) added HBr to form a compound, m. 89-90°, C8H13BrO2, and Br2 to form C4H12Br2O2 m. 133-34°. Oxidized with permanganate, cyclohexanone was formed. The isomeric acid, m. 38°, probably structure I, yielded the same compound as the Δ1.7-acid and the hexanolacetic acid with halogen hydrides. Monochlorcyclohexylacetic acid, m. 83°. Monobromcyclohexylacetic acid, m. 89-90°. Monoiodocyclohexylacetic acid, m. 99-100°. The acid, m. 38°, added two atoms bromine to form a compound, m. 119-20°, and distilled with sulphuric acid yielded a lactone. The acid chloride and the amide, m. 152-53°, were prepared. On oxidation, no definite products could be identified. Cyclohexylacetic acid, b. 245-47°, m. 30-31°, was prepared by reduction (Zn dust and acetic acid) of the brom- or iodo- acid. Amide, m. 168°. Nitrile, b. 215-17°, on reduction yielded, β-cyclohexylethylamine, b. 188-189°. Hydrochloride, m. 252-53°; chlorplatinate, m. 253-54°; ureide, m. 85-86°; methylammonium iodide, m. 221-22°. Cyclohexylmethylamine, b. 162-164°, was prepared from the amide, bromine and alkali. Hydrochloride, m. above 210°. Chlorplatinate, m. 240° (decompose). Ureide, m. 170-72°. Cyclohexylacetic acid distilled with lime yielded the completely hydrated dibenzylketone. Semicarbazone, m. 142-45°. Similarly cyclohexylacetone, b. 198-200°, was prepared. Semicarbazone, m. 165-66°. II Suberone derivatives. The methods used were the same as before. Suberylacetic acid, (cycloheptylacetic acid), b10 165°. Silver salt. Amide, m. 146-48°. Amine, b. 193-95°, [n]D=1.4719, hydrochloride, m. 229-32°; chlorplatinate; ureide, m. 127-29°; trimethylammonium iodide, m. 223°. III Cyclopentanone derivatives. Cyclopentylacetic acid, b. 226-30°. Amide, m. 143-45°. Amine, b. 139-45°; hydrocldoride, chlorplatinate. Cyctopentanone and ethyl α-isobrombutyrate condensed with zinc formed pentanolisobutyric ester, b11 108-13°, which lost water on heating with potassium acid sulphate and yielded cyclopenteneisobutyric acid, b11 148-50°. Silver salt. HCl was added readily to form monochlorcyclopentylisobutyric acid, m. 122.5-123.5°. Monobromcyclopentylisobutyric acid, m. 113-14°. Moniodocyclopentylisobutyric acid, m. 107-108°. The dry distillation of the pentene isobutyric acid yielded a hydrocarbon, C14H8, b. 136-37° probably chiefly, since on oxidation cyclopentanone (semicarbazone) was formed. An isomer, was also formed and could also be obtained from the first on prolonged heating with alcoholic sulphuric acid. IV 1,4-Methylcyclohexonone derivatives. (Edgar Evans). 1,4-Methylhexeneacetic acid, (Ibid., 343, 345) CH3C6?H9:CH.CO2H, m. 42-43°. Monochlorcyclomethylhexylacetic acid, m. 88-89°. Monobromcyclomethylhexylacetic acid, m. 85-86°. Dibromcyclomethylhexylacetic acid, m. 97-99°. Cyclomethylhexeneacetomide, m. 155-56°. Nitrile, b15 107°, 1,4-Cyclomethylhexylacetic acid, m. 63-65°. Amide, m. 161-62°. V Menthone derivatives (Eduard Schellack). Menthone condensed with methylbromacetate and zinc yielded mentholacetic acid methyl ester, , m. 32-33°, b.10 136-137°. Acid, m. 82-83°, b11 193-197°. Brommenthylacetic acid. In the preparation of mentheneacetic acid, a lactone, C12H20O2, b. 300-305°, [n]D=1.4781 at 22°, was obtained, which, on boiling with HI and phosphorus yielded a substance, m. 88.5-89.5°, isomeric with the lactone. The liquid lactone was levorotatory, the solid, dextrorotatory. Brommenthylacetic acid reduced gave menthylacetic acid, b11 166-170°. Amide, m. 148-150°. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Name: 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. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Name: 2-Cyclohexylacetonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts