2,4-Dihydroxybenzaldehyde → HCID 10537643, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2,4-dihydroxybenzaldehyde (42.6 g) in dimethylformamide (250 mL) at ambient temperature is treated with sodium hydride (13.5 g; 60% w/v dispersion in mineral oil; 338 mmol), portionwise during 30 minutes. It is then treated with 3-chloromethylthiophene and the reaction mixture is heated at 60° C. for 3 hours. The mixture is concentrated in vacuo and the residue is partitioned between hydrochloric acid (200 mL; 0.5 N) and ethyl acetate (200 mL). The aqueous layer is extracted with ethyl acetate (3×100 mL) and the combined organic extracts are washed with brine (50 mL), dried over magnesium sulphate, filtered and the solvent is removed in vacuo. Flash chromatography on silica gel, using a mixture of petroleum ether (b.p. 40-60° C.) and ethyl acetate (4:1 v/v) as eluent, gives 2-hydroxy-4-(3-thienylmethoxy)benzaldehyde (11.8 g), in the form of a white solid.

Provenance & Evidence