Anthraquinone → HCID 22138024, compound

HRID 901747Notes

Reaction equation

HRID 901747 reaction equation
BrC1C=CC=CC=1[C:8]1[C:21]2[C:22]3=[C:23]4[C:18](=[CH:19][CH:20]=2)[CH:17]=[CH:16][CH:15]=[C:14]4[CH:13]=[CH:12][C:11]3=[CH:10][CH:9]=1.[CH2:24]([Li])[CH2:25][CH2:26][CH3:27].[CH:29]1[C:42]2[C:41](=[O:43])[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34](=[O:44])[C:33]=2[CH:32]=[CH:31][CH:30]=1.[Cl-].[NH4+].[CH3:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]>C1COCC1.C1(C)C=CC=CC=1>[C:24]1([C:8]2[CH:21]=[CH:22][C:11]([C:41]3([OH:43])[C:40]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[C:34]([C:14]4[CH:23]=[CH:18][C:17]([C:8]5[C:21]6[C:22]7=[C:23]8[C:18](=[CH:19][CH:20]=6)[CH:17]=[CH:16][CH:15]=[C:14]8[CH:13]=[CH:12][C:11]7=[CH:10][CH:9]=5)=[CH:16][CH:15]=4)([OH:44])[C:33]4[C:42]3=[CH:29][CH:30]=[CH:31][CH:32]=4)=[CH:10][CH:9]=2)[C:52]2[C:47]3=[C:48]4[C:49](=[CH:50][CH:51]=2)[CH:52]=[CH:51][CH:50]=[C:49]4[CH:48]=[CH:47][C:27]3=[CH:26][CH:25]=1

Participants

8

Reactant 5

HCID 6780AnthraquinoneHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 22138044HCID 22138044, compoundHCID 178418339Butyllithium

Product 1

HCID 22138024HCID 22138024, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

Under an atmosphere of argon, 1-(2-bromophenyl)pyrene (6.6 g, 18 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 obtained solution was stirred at −20° C. for 1 hour. To the obtained mixture, 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 and washed with water, methanol and acetone and a white solid (4.5 g, 88%) was obtained.

Workup

  1. waitleft
  2. waitstanding for one night
  3. customTo the obtained reaction mixture
  4. customThe formed solid was separated by filtration
  5. washwashed with water, methanol and acetone

Sources & evidence

ORD record
ord-424c72c36b9042639bae8f321a007f8c
Source dataset
uspto-grants-2008_04
Patent number
US07361796B2

Reaction notes

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