Sodium borohydride → 4-(1-Octynyl)benzyl alcohol

Participants

Reaction Steps

To a solution of 4-(1-octynyl)benzaldehyde (15 g, 0.07 mole from example 4) in ethanol (200 ml) was added sodium borohydride (1.32 g, 0.035 mole) in ethanol and the mixture was stirred for 5 minutes until no further aldehyde remained. The solution was concentrated, ether was added and the solution was washed with water and dried (MgSO4). Evaporation gave an oil which was chromatographed on silica eluting with dichloromethane to give 12.5 g (82%) of the alcohol as an oil, νmax (film) 815, 840, 1020, 1040, 1510, 2220, 3300 cm-1 ; δ(CDCl3) 0.88 (3H, distorted t, terminal CH3), 1.1-1.8 (8H, m, alkylene chain), 2.2 (1H exchangeable, OH), 2.36 (2H, t, J 7 Hz, CH2 --C≡C), 4.56 (2H, s, CH2O), 7.3 (4H, ABq, aromatics). M+ 216.1524 (C15H20O requires, 216.1514).

Provenance & Evidence