Water → HCID 70983867, compound

Participants

Reaction Conditions

Reaction Steps

A 100 mL 3-neck flask was equipped with a magnetic stirrer, a reflux condenser, a nitrogen blanket, and a heating mantle with a temperature controller and a thermocouple. The flask was charged with o-phenylphenol (6.83 grams, 0.04 moles), with KOH (2.63 grams, 0.04 moles), and with 25 mL of DMSO. The mixture was stirred at about 35° C. for about ¾ hour, then a solution of α,α′-dichloro-m-xylene (3.52 grams, 0.02 moles) in 5 mL of DMSO was added to the dark solution over about 25 minutes. After the addition, the reaction mixture was heated at 50° C. for about 3 hours, and then it was poured into about 400 mL of water. A sticky white solid separated. The mixture was slurried with about 75 mL of diethyl ether; the solids dissolved. The mixture was transferred to a separatory funnel, and the layers were separated. The aqueous layer was extracted with 2×75 mL of diethyl ether. The ether layers were combined and were washed with 1×75 mL of saturated aqueous sodium chloride solution, and then they were dried over anhydrous magnesium sulfate. After filtration, the ether was removed by rotary evaporation at a bath temperature of about 60° C./P=3.4 kPa to give 8.42 grams of clear, viscous brown oil. Yield=95%. Structure was confirmed by IR, GC/MS, and 1H- and 13C-NMR analyses.

Provenance & Evidence