Anthraquinone → 9,10-Bis(2-(1-naphthyl)phenyl)-9,10-dihydroxy-9,10-dihydroanthracene

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Reaction Steps

Under an atmosphere of argon, 1-(2-bromophenyl)naphthalene (5.4 g, 19 mmole, 2.8 eq) was dissolved into a mixed solvent composed of anhydrous toluene (25 ml) and anhydrous THF (25 ml) and the resultant solution was cooled at −40° C. in a dry ice/methanol bath. To the cooled solution, a hexane solution of n-butyllithium (1.50 mole/liter, 14 ml, 21 mmole, 1.1 eq) was added and the resultant solution was stirred at −20° C. for 1 hour. To the obtained solution, anthraquinone (1.4 g, 6.7 mmole) was added and the resultant mixture was stirred at −20° C. for 1 hour and at the room temperature for 3 hours and left standing for one night. To the obtained reaction mixture, a saturated aqueous solution of ammonium chloride (20 ml) was added. The formed solid was separated by filtration, washed with water, methanol and acetone and a white solid (3.5 g, 85%) was obtained.

Provenance & Evidence