Phenol → HCID 13776066, compound

Participants

Reaction Conditions

Reaction Steps

Tetrakis(triphenylphosphine)palladium (0.4 g, 0.35 mmol) and phenol were dissolved in 70 mL THF and the solution was cooled to 0° C. Butadiene monoxide (5.5 mL, 50 mmol) was then added, and the reaction was allowed to warm to room temperature. After 2 hours at room temperature, GLC analysis indicated that phenol was no longer present, and that two products were obtained in a 1:4 ratio (1-hydroxy-4-phenoxy-but-2-ene: 4-hydroxy-3-phenoxy-but-1-ene). The solvent and excess butadiene monoxide were removed at reduced pressure, and the residue was chromatographed on silica gel (ether:hexane; 1:1 eluant) giving pure samples of each product in a combined yield of 91%.

Provenance & Evidence