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

HRID 2413647Notes

Reaction equation

HRID 2413647 reaction equation
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

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 947NitrogenHCID 8270310-Chloro-9-anthraldehydeHCID 23665647Potassium tert-butoxide2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 3 L 2-neck flask fitted with thermometer, condenser, stirring bar, N2 line and bubbler was charged with KOtBu (MCB, 25 g, 0.22 mol), 1,2-ethylene glycol (Fisher, 1.5 L) 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 poured into cold H2O (1.5 L), then stirred for 10 min before the precipitate was collected by filtration. The yellow solid was dissolved in CH2Cl2 (1 L) and passed through a plug of SiO2 (100 g) using CH2Cl2 (9 L) as the eluting solvent. 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°) 28.82 g (53%), 10-(2-hydroxyethyloxy)-9-anthracenecarbaldehyde mp 142°-144°, (CH2Cl2 /hexane), (C, H).

Workup

  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 min before the precipitate
  5. filtrationwas collected by filtration
  6. dissolutionThe yellow solid was dissolved in CH2Cl2 (1 L)
  7. washThe desired material was then eluted with EtOAc (12 L)
  8. customthe solvent removed
  9. customto give
  10. dry with material(after drying at 50°) 28.82 g (53%), 10-(2-hydroxyethyloxy)-9-anthracenecarbaldehyde mp 142°-144°, (CH2Cl2 /hexane), (C, H)

Sources & evidence

ORD record
ord-45c430cce03747baa04aace19b1410ad
Source dataset
uspto-grants-1988_01
Patent number
US04719049

Reaction notes

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