3-(Carboxymethyl)-2-chlorobenzoic acid → 2-Chloro-3-(2-hydroxyethyl)benzaldehyde

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Reaction Steps

Manganese (IV) dioxide (43.1 g) was added to a slight suspension of 2-(2-chloro-3-(hydroxymethyl)phenyl)ethanol [Aromatic Intermediate 11, step d] (18.5 g) in chloroform (500 mL), and the resulting suspension was heated at reflux for 2 h. The reaction mixture was cooled, filtered through Celite and the filter pad washed with DCM (3×300 mL). The combined washings and filtrate were evaporated and the residue purified by flash silica chromatography eluting with 3:1 to 1:1 isohexane:ethyl acetate gradient. The fractions containing product were combined and evaporated to give the titled compound as a white solid. Yield 12.00 g.

Provenance & Evidence