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

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Reaction Steps

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).

Provenance & Evidence