Quinizarin → 1,4-Bis(octyloxy)anthracene-9,10-dione

HRID 525979

反応式

HRID 525979 の反応式
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5](O)=[CH:4][CH:3]=1.Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[C:28](=[O:31])([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:20]([O:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([O:31][CH2:28][CH2:14][CH2:15][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:4][CH:3]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

参加物

5

反応物 3

HCID 6688QuinizarinHCID 81401-BromooctaneHCID 11430Potassium Carbonate2 回

生成物 1

HCID 684413171,4-Bis(octyloxy)anthracene-9,10-dione収率 37.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1,4-dihydroxyanthracene-9,10-dione (5.0 g, 20.6 mmol), 1-bromooctane (10.0 g, 51.8 mmol), and potassium carbonate (37 g, 0.268 mol) was mixed in N,N-dimethylformamide and heated at 90° C. for 7 h after which the potassium carbonate was filtered off. The reaction mixture was quenched with water and extracted three times with ether. The ether was then washed three times with 1M HCl, one time with water, and evaporated to give a dark yellow solid. This solid was recrystallised in methanol to yield 1,4-bis(octyloxy)anthracene-9,10-dione (1.81 g, 3.88 mmol) as a yellow solid. 1H-NMR (CDCl3, δ): 0.89 (t, 6H), 1.2-1.4 (m, 16H), 1.53 (m, 4H), 1.93 (m, 4H), 4.10 (t, 4H), 7.30 (s, 2H), 7.71 (m, 2H), 8.16 (m, 2H) MS MALDI-TOF (m/z): 464.328

後処理

  1. filtrationwas filtered off
  2. customThe reaction mixture was quenched with water
  3. extractionextracted three times with ether
  4. washThe ether was then washed three times with 1M HCl, one time with water
  5. customevaporated
  6. customto give a dark yellow solid
  7. customThis solid was recrystallised in methanol

出典と根拠

ORDレコード
ord-555a9ae8fe2840619383765dd74b0a95
出典データセット
uspto-grants-2016_05
特許番号
US09343198B2

関連ノート

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