Hydrochloric Acid → 2-Butylhexanol

Participants

Reaction Steps

Compound 16 (54.1 g, 270 mmol) was dissolved in anhydrous THF (450 mL) and cooled in an ice/water bath under nitrogen protection. Lithium aluminum hydride (LAH) (15.3 g, 404 mmol) was added into the reaction flask in small portions. The temperature of the reaction solution was increased to room temperature and then refluxed overnight. The reaction mixture was cooled down to room temperature and poured very slowly into the ice/water solution. The solution was acidified using a 2N HCl aqueous solution, extracted with Et2O (150 mL×3), and then concentrated via rotary evaporation. The resulting crude oil was purified via vacuum distillation. The compound 17 was collected as colorless oil (32.6 g, 76.2%). 1H NMR (CDCl3): δ 0.87-0.92 (6H, m), 1.17-1.42 (12H, m), 1.40-1.50 (1H, m), 3.53 (2H, d). MS (EI): calcd, 158.3. found M+H+, 159.2.

Provenance & Evidence