Reaktion #988936

Reaktionsgleichung

n-butyllithium

2-(4-bromophenyl)naphthalene

anthraquinone

ammonium chloride

→

solid

Ausbeute 91.0%

9,10-bis(4-(2-naphthyl)phenyl)-9,10-dihydroxy-9,10-dihydroanthracene

Ausbeute 91.0%

Lösungsmittel

hexane

toluene

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITleft
2. 2
   workup.WAITstanding for one night
3. 3
   SonstigeTo the obtained reaction mixture
4. 4
   SonstigeThe formed solid was separated by filtration
5. 5
   Waschenwashed with water, methanol and acetone

Vorschrift

Under an atmosphere of argon, 2-(4-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 mixture was stirred at −20° C. for 1 hour. To the resultant solution, anthraquinone (1.4 g, 6.7 mmole) was added and the obtained 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 and washed with water, methanol and acetone and a white solid (3.7 g, 91%) was obtained.

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