2,4-Dihydroxybenzaldehyde → HCID 10537643, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 2,4-dihydroxybenzaldehyde (31.8 g) in dry dimethylformamide (150 mL) at ambient temperature is treated with sodium hydride (11.96 g; 60% w/v dispersion in mineral oil; 300 mmol), portionwise, during 30 minutes. After a further period of 15 minutes, the mixture is treated, dropwise, with a solution of 3-chloromethylthiophene (35 g) in dimethylformamide (50 mL). The mixture is stirred at 70° C. for 2 hours, then it is cooled and the solvent is evaporated. The residue is partitioned between ethyl acetate (200 mL) and hydrochloric acid (200 mL; 0.5 M), and the aqueous layer is extracted further with ethyl acetate (2×100 mL). The combined organic extracts are washed with brine (100 mL), dried over magnesium sulphate, and concentrated in vacuo. The residue is subjected to flash chromatography on silica gel, eluting with a mixture of ethyl acetate and pentane (1:4 v/v), to give a colourless oil, which crystallises on standing. This solid is recrystallised from diisopropyl ether, to give 2-hydroxy-4-(3-thienylmethoxy)benzaldehyde (8 g), in the form of a white solid.

Provenance & Evidence