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Hydrochloric Acid → 2,10-Di(2-naphthyl)anthracene

HRID 68528
ノート
印刷プレビュー

反応式

HRID 68528 の反応式
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.C([Li])CCC.[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[C:27]1[CH:40]=[CH:39][C:38]2[C:37](=O)[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:30][C:29]=2[CH:28]=1.Cl>C1COCC1.CCCCCC>[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[C:27]1[CH:40]=[CH:39][C:38]2[C:29](=[CH:30][C:31]3[C:36]([C:37]=2[C:2]2[CH:11]=[CH:10][C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH:3]=2)=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:28]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 113722-BromonaphthaleneHCID 581944502-(2-Naphthyl)-10-anthroneHCID 178418339Butyllithium

生成物 1

HCID 581942762,10-Di(2-naphthyl)anthracene収率 32%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回
HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

Under an argon atmosphere, a solution of 4.81 g of 2-bromonaphthalene in 30 mL of THF was cooled to −78° C. Subsequently, 25 mL of a 1.6-M solution of n-butyllithium in hexane were dropped to the solution, and then the mixture was stirred at −78° C. for 1 hour. A solution of 6.76 g of 2-(2-naphthyl)-10-anthrone in 20 mL of THF was added to the mixture, and then the resultant reaction solution was stirred for 5 hours at 50° C. under heat. After the reaction solution had been cooled to room temperature, 100 mL of 10% hydrochloric acid were added to the solution. After the water layer had been removed, the organic layer was washed with water and a saturated salt solution. Then, the organic layer was dried with magnesium sulfate. The solvent was removed by distillation under reduced pressure, and then the residue was purified by silica gel column chromatography. Thus, 2.90 g of 2,10-di(2-naphthyl)anthracene were obtained (in 32% yield).

後処理

  1. customthe resultant reaction solution
  2. stirringwas stirred for 5 hours at 50° C.
  3. temperatureunder heat
  4. temperatureAfter the reaction solution had been cooled to room temperature
  5. customAfter the water layer had been removed
  6. washthe organic layer was washed with water
  7. dry with materialThen, the organic layer was dried with magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure
  9. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-9b4acf6cbeac4810b14a951005e380ec
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822041B2

反応ノート

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