Hydrochloric Acid → HCID 14750108, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 46.94 g (0.338 mol) of 4-formylheptanenitrile in 250 mL of methanol at 3° C., under argon, was added 4.55 g (0.120 mol) of sodium borohydride portionwise over 1 hr. After stirring at 5° C. for 1 hr, the reaction mixture was poured into a mixture of 100 g of ice and 200 mL of 2N hydrogen chloride solution and extracted with 500 mL followed by 4×250 mL of ether. The combined extracts were washed with 2×150 mL of saturated brine, dried (Na2SO4), filtered and concentrated. The residue was dried (40° C./1.0 mm Hg) to give 45.50 g (95.6%) of crude 4-(hydroxymethyl)heptanenitrile; TLC ((SiO2, 1:1 ethyl acetate:hexane) Rf 0.28 (PMA); IR (chloroform): μmax 3625 (OH), 3490 (OH), 2245 (C≡N) cm-1.

Provenance & Evidence