Pyridine → 2-Nitrobenzeneacetaldehyde

Participants

Reaction Steps

Trifluoroacetic acid (1.31 ml, 17 mmols) and 2.7 ml (33.3 mmols) of pyridine were added to a mixture of 5.51 g (33.3 mmols) of 2-(2-nitrophenyl)ethanol, 50 ml of dimethyl sulfoxide, 50 ml of benzene and 21 g (0.1 mol) of DCC. After stirring the mixture at room temperature for 4 hours, 300 ml of aqueous solution of 8.82 g (70 mmols) of oxalic acid dihydrate was added thereto. The resulting mixture was stirred at room temperature for 30 minutes and diluted with 500 ml of ethyl acetate. The organic layer was separated off, washed with saturated NaCl, dried over Na2SO4 and concentrated to obtain a yellow oil. The oil was subjected to silica gel column chromatography (95:5 benzene-ethyl acetate) to obtain 2-nitrophenylacetoaldehyde in the form of an unstable oil in an amount of 4.50 g (yield 81%).

Provenance & Evidence