Ethylene Glycol → 10-(2-Hydroxyethoxy)-9-anthracenecarbaldehyde

HRID 2413622

반응식

HRID 2413622 반응식
N#N.CC([O-])(C)C.[K+].[CH2:9]([OH:12])[CH2:10][OH:11].Cl[C:14]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH:28]=[O:29])=[C:20]2[C:15]=1[CH:16]=[CH:17][CH:18]=[CH:19]2>O>[OH:11][CH2:10][CH2:9][O:12][C:14]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH:28]=[O:29])=[C:20]2[C:15]=1[CH:16]=[CH:17][CH:18]=[CH:19]2

참가 물질

6

반응물 4

HCID 174Ethylene GlycolHCID 947NitrogenHCID 8270310-Chloro-9-anthraldehydeHCID 23665647Potassium tert-butoxide2회

생성물 1

HCID 1337540510-(2-Hydroxyethoxy)-9-anthracenecarbaldehyde

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A 3-L 2-neck flask fitted with thermometer, condenser, stirring bar, N2 line and bubbler was charged with KOtBu (MCB Manufacturing Chemists, Inc., 2909 Highland Ave., Cincinnati, OH, 45212, 25 g, 0.22 mol), ethyleneglycol (1500 mL) and 10-chloro-9-anthraldehyde (Aldrich, 50 g, 0.207 mol). The mixture was stirred at 100° for 1.5 h. An additional 5 g (45 mmol) of KOtBu was added and the stirring continued for an additional 0.5 h. The reaction mixture was cooled and poured into 1500 mL of cold H2O, stirred for 10 minutes before the precipitate was collected by filtration. The yellow solid was dissolved in 1 L of CH2Cl2 and passed through a 100 g plug of SiO2 using CH2Cl2 (9 L). The CH2Cl2 contained impurities only and was discarded. The desired material was then eluted with EtOAc (12 L). The appropriate fractions were combined and the solvent removed to give after drying at 50° 10-(2-hydroxyethyloxy)-9-anthracenecarbaldehyde 28.82 g (53%), mp 142°-144°, (CH2Cl2 /hexane), (C,H).

후처리

  1. customA 3-L 2-neck flask fitted with thermometer, condenser
  2. stirringThe mixture was stirred at 100° for 1.5 h
  3. temperatureThe reaction mixture was cooled
  4. stirringstirred for 10 minutes before the precipitate
  5. filtrationwas collected by filtration
  6. dissolutionThe yellow solid was dissolved in 1 L of CH2Cl2
  7. washThe desired material was then eluted with EtOAc (12 L)
  8. customthe solvent removed
  9. customto give
  10. dry with materialafter drying at 50° 10-(2-hydroxyethyloxy)-9-anthracenecarbaldehyde 28.82 g (53%), mp 142°-144°, (CH2Cl2 /hexane), (C,H)

출처 및 근거

ORD 기록
ord-7a531a86d91f4aa4ae48c17ead6aefa0
출처 데이터셋
uspto-grants-1988_01
특허 번호
US04719047

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