Ammonium Chloride → 3,3-Dimethylhex-5-en-1-ol

Participants

Reaction Conditions

Reaction Steps

In a 1-L 4-necked round-bottom flask, 3,3-dimethylhex-5-enal (14.20 g; 0.113 mol) was dissolved in absolute ethanol (420 mL). Then the mixture was cooled to 5° C. in an ice-bath and, under nitrogen atmosphere, sodium borohydride (3.3 g; 0.087 mol) was added cautiously in 10 minutes. After the mixture had been stirred for 1 hour, it was poured into 5% ammonium chloride, diluted with water, and extracted with dichloromethane. Extracts were dried over sodium sulfate and evaporated, then the white solid was filtered away, while the pale yellow oil was distilled at 55-56° C. (4 mmHg) to give the title compound as a foul smelling, colorless liquid.

Provenance & Evidence