Synthesis
GENERAL STEPS: A mixture of benzeneacetonitrile (50.0 g, 426.8 mmol) and 1,5-dibromopentane (58.1 mL, 426.8 mmol) was added slowly and dropwise to a dimethylsulfoxide (600.0 mL) suspension of NaH (42.7 g, 1067.0 mmol, 60%) at 0 °C. The mixture was pre-dissolved in a solvent mixture of dimethyl sulfoxide and ether (1:1, 200.0 mL). After dropwise addition, the reaction mixture was continued to be stirred at 0°C for 2 hours. Upon completion of the reaction, water and 10% HCl solution were added to the mixture, followed by extraction with ethyl acetate. The organic layers were combined, washed sequentially with water and brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the crude product. The crude product was purified by conventional silica gel column chromatography (eluent: hexane) to afford 1-phenyl-1-cyclohexanecarbonitrile (52.0 g, yield 65.76%) as a colorless oil.GC-MS analysis showed that the molecular ion peak m/z was 185.0.
References
[1] Patent: US2014/194431, 2014, A1. Location in patent: Paragraph 0940-0942
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3913 - 3924
[3] Journal of Organic Chemistry, 1971, vol. 36, p. 1308 - 1309
[4] Chemische Berichte, 1973, vol. 106, p. 2890 - 2903
[5] Bulletin de la Societe Chimique de France, 1965, p. 2030 - 2037
