Acetone → HCID 57591432, compound

Participants

Reaction Steps

18 g (0.11 mol) of 6,8-dimethylnon-7-enal (1) and 96.0 g of ethanol are placed in a 500 ml round-bottomed flask equipped with a thermometer. Cooling is carried out to 5° C. and 2.0 g of sodium borohydride are added in small portions without exceeding a bulk temperature of 10° C. The mixture is stirred at ambient temperature for 16 hours. Cooling is carried out to 5° C. and 20.0 g (1.36 mol) of acetone are added dropwise to destroy the excess reducing agent without exceeding a bulk temperature of 10° C. The reaction medium is acidified with 20.0 g of 10% hydrochloric acid without exceeding a bulk temperature of 10° C. 40 g of water are also added, followed by 70 g of toluene, with vigorous stirring. The phases are separated and the organic phase is washed once with 50 g of saturated aqueous NaHCO3 solution and twice with 50 g of water. The organic phase is dried and filtered, and the toluene is evaporated at reduced pressure. After distillation, 13.4 g (0.08 mol) of (B.p.: 105° C./10 torr) are obtained. The yield is 72.7%. The analyses of the infrared, NMR and mass spectra correspond to the expected alcohol.

Provenance & Evidence