Sodium Hydroxide → HCID 18783157, compound

To a vigorously stirred solution of 1,3,3,5,5-pentamethylcyclohexanoi (3-13) (2.7 g, 15.6 mmol) and trimethylsilyl cyanide (2.36 g, 23.8 mmol) in acetic acid (2.5 ml) under argon 98% sulfuric acid (4.66 g, 47.6 mmol) was added, keeping temperature below -5° C. The mixture was stirred at room temperature for 22 h, then it was poured onto ice (100 g), neutralised with 50% NaOH solution to pH ~7 and extracted with ether (3*30 ml). The combined ether phases were washed with saline (50 ml), then dried over MgSO4 and evaporated. A slightly yellow crystalline residue was treated with small amount of acetonitrile and filtered off to give 2.5 g (80%) of 14-1 as a white crystals, m.p. 104-106° C. 1H NMR (CDCl3, TMS) δ: 0.91 and 0.93 (total 6H, both s, 3,5-CH3eq); 1.08 (2H, m, 2,6-CHeq); 1.13 and 1.15 (total 6H, both s, 3,5-CH3ax); 1.25 (2H, m, 4-CH2); 1.32 and 1.38 (total 3H, both s, 1-CH3); 1.70 and 2.12 (total 2H, both d, 14.7 Hz, 2,6-CHax); 5.30 and 5.60 (total 1H, both br s, NH); 8.05 and 8.30 ppm (total 1H, both d, 2.0 and 12.7 Hz, resp., HCO).