2-Methoxyethanol → 10-(2-Methoxyethoxy)9-anthracenecarbaldehyde

Participants

Reaction Steps

A mixture of KOtBu (MCB, 18.2 g, 0.162 mol)) in 2-methoxyethanol (1 L) was treated with 10-chloro-9-anthraldehyde (Aldrich, 25 g, 0.104 mol) and refluxed for 2 h. The cooled reaction mixture was diluted with H2O (5 L), and the resulting oil stirred for 2 h until solidification occurred. The filtered solid was chromatographed on a plug of SiO2 (500 g) using CH2Cl2 as the eluting solvent to afford 26.9 g (92%) of 10-(2-methoxyethoxy)-9-anthracenecarboxaldehyde mp 87°-88°, (C, H), (CH2Cl2 /hexane).

Provenance & Evidence