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

HRID 525979

반응식

HRID 525979 반응식
[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]

참가 물질

5

반응물 3

HCID 6688QuinizarinHCID 81401-BromooctaneHCID 11430Potassium Carbonate2회

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-555a9ae8fe2840619383765dd74b0a95
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09343198B2

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