Ammonium Hydroxide → 3-Octanol

To a well-stirred solution of 19.2 g (0.15 mmol) of 3-octanone in 270 ml of 95% ethanol, cooled in an ice bath, was added in portions a solution of 3.9 g (0.103 mmol) of sodium borohydride in 27 ml of water. Ammonium hydroxide (15M, 27 ml) was added and the ice bath removed and stirring was continued in room temperature for 3 hr. The reaction mixture was concentrated to near dryness and the residue was partitioned between 250 ml each of CHCl3 and H2O. The organic layer was separated and the aqueous layer was extracted with CHCl3 (2×200 ml). The combined extracts were washed with 5% HCl (350 ml), and saturated NaCl solution (350 ml) and dried over MgSO4. After the removal of the solvent, the liquid residue was distilled under reduced pressure (bp 86°-87° C./24 Torr; lit. bp 69.5°-70.4° C./7 Torr (18)) to give 15.41 g (79.02%) of pure 3-octanol. NMR(CDCl3): δ0.93 (6H, t, CH3), δ1.37 (10H, broad multiplet, --CH2 --), δ2.35 (1H, broad singlet, exchangeable with D2O and shift to low field in pyridine, --OH), δ3.47 (1H, m, >CHO--).