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

HRID 901740
ノート
印刷プレビュー

反応式

HRID 901740 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 1140
Toluene
溶媒
HCID 8028Tetrahydrofuran溶媒
HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b46859c1171e4a9eaa25e1b8f626d801
出典データセット
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07361796B2

反応ノート

読み込み中…

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