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

참여 물질

반응 단계

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).

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