Water → trans-3-Octen-1-ol

Participants

Reaction Steps

LiAlH4 (13.5 mL, 13.5 mmol, 1 M/THF) was added to an ice cold solution of (E)-oct-3-enoic acid (7-1, 1.86 g, 13.1 mmol) in THF (48 mL). The reaction was allowed to warm to room temperature and after 2 h, was cooled in an ice bath and 50 mL H2O was added slowly. NaOH (3 M, 50 mL) and H2O (50 mL) were added and the resulting mixture was extracted with dichloromethane (3×100 mL). The combined organic layer was washed with brine (100 mL) and was then dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (Isco Combiflash unit) gave the title compound (1.283 g, 76%).

Provenance & Evidence