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

HRID 901740
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 901740
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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140
Toluene
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b46859c1171e4a9eaa25e1b8f626d801
Quelldatensatz
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07361796B2

Notizen zur Reaktion

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