Dimethylformamide → 6-Methoxysalicylaldehyde

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Reaction Steps

The 3-(1-ethoxyethoxy)anisole was dissolved in ether (750 ml) and n-butyllithium (1.6M solution in hexanes; 500 ml) was added dropwise at ambient temperature under nitrogen. The mixture was stirred at ambient temperature for 2 hours, then it was cooled to 10° C. and a solution of dimethylformamide (94 g) in ether (150 ml) was added dropwise. The mixture was stirred at ambient temperature for 2 hours, then poured onto crushed ice. The product was extracted into ether, the combined extracts dried over magnesium sulphate, and the solvents removed in vacuo. The residual oil was dissolved in methanol (500 ml) and the stirred solution was cooled in ice and made strongly acidic by the addition of hydrochloric acid (2M). The resulting solid was collected by filtration, washed with water, dried in vacuo over phosphorus pentoxide and crystallised from petroleum ether (b.p. 60°-80° C.) to give 2-hydroxy-6-methoxybenzaldehyde as pale yellow needles (16 g), m.p. 69°-71° C.

Provenance & Evidence