Sodium Cyanide → HCID 57904789, compound

Participants

Reaction Steps

To a stirred solution of NH4OH (125 mL) and methanol (50 mL) was added 4-(hydroxymethyl)cyclohexanone (10 g, 78 mmol), NH4Cl (8.35 g, 156 mmol) and NaCN (7.65 g, 156 mmol). After 16 h at room temperature, the reaction mixture was extracted with CH2Cl2 (250 mL×2), and 4:1 chloroform:2-propanol, and the combined organic fractions washed with water (500 mL), dried (Na2SO4), filtered and concentrated to afforded the title compound as a colorless liquid (8 g, 67% yield). 1H NMR (500 MHz, CDCl3) δ: 3.51 (d, 2H, J=4.58 Hz), 2.07-2.09 (m, 2H), 1.86-1.91 (m, 4H), 1.68 (s, 2H), 1.47-1.53 (m, 3H), 1.41 9 brs, 1H), 1.30-1.36 9 m, 2H). LCMS (M+H)=155.18.

Provenance & Evidence