1,4-二羟基蒽醌 → 1,4-Bis(octyloxy)anthracene-9,10-dione

HRID 525979

反应方程式

HRID 525979 反应方程式
[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]

参与物

5

反应物 3

HCID 66881,4-二羟基蒽醌HCID 81401-溴辛烷HCID 11430碳酸钾2 次

产物 1

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

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

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

后处理

  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

来源与证据

ORD记录
ord-555a9ae8fe2840619383765dd74b0a95
来源数据集
uspto-grants-2016_05
专利号
US09343198B2

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