3-Phenylprop-2-En-1-Ol → HCID 12561033, compound

Participants

Reaction Steps

Sodium hydride (60% in mineral oil, 26 g, 0.60 mol) was added portion-wise to a solution of cinnamyl alcohol (40 g, 0.29 mol) in dry THF (600 ml) at 5° C. under nitrogen. The reaction was warmed up to room temperature then refluxed. After 30 minutes, tetra butyl ammonium iodide (4 g, 0.011 mol) was added followed by allyl chloride (45.6 g, 0.60 mol) over a 1 h-period. The reaction was allowed reaching room temperature overnight, before being poured onto water. The organic phase was washed with water (3 times) and brine. Each aqueous phase was re-extracted with heptanes. Combined extracts were dried over solid anhydrous sodium sulfate. The solid was filtered off, rinsed with heptanes and the solvents were removed under vacuum. The product was purified by bulb-to-bulb distillation (80° C./0.062 mbar). 50 g of the desired compound were obtained (0.287 mol, 99%).

Provenance & Evidence