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

HRID 901740
Notes
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Reaction equation

HRID 901740 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1.[CH2:18]([Li])[CH2:19][CH2:20][CH3:21].[CH:23]1[C:36]2[C:35](=[O:37])[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28](=[O:38])[C:27]=2[CH:26]=[CH:25][CH:24]=1.[Cl-].[NH4+]>CCCCCC.C1COCC1.C1(C)C=CC=CC=1>[C:21]1([C:8]2[CH:17]=[CH:12][CH:11]=[CH:10][C:9]=2[C:35]2([OH:37])[C:34]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:28]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:8]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH:11]=[CH:10][CH:9]=3)([OH:38])[C:27]3[C:36]2=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:7]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:18]=[CH:19][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6780AnthraquinoneHCID 25517Ammonium ChlorideHCID 118329071-(2-Bromophenyl)naphthaleneHCID 178418339Butyllithium

Product 1

HCID 221380349,10-Bis(2-(1-naphthyl)phenyl)-9,10-dihydroxy-9,10-dihydroanthraceneYield 85%

Reagents, catalysts & solvents 3

HCID 1140
Toluene
Solvent
HCID 8028TetrahydrofuranSolvent
HCID 8058HexaneSolvent

Procedure

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.

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-b46859c1171e4a9eaa25e1b8f626d801
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07361796B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes