4-Hydroxybenzaldehyde → 4-[(2,6-dichlorobenzyl)oxy]benzaldehyde

Participants

Reaction Steps

To a solution of 4-hydroxybenzaldehyde (3.59 g, 24.39 mmol) and 2,6-dichlorobenzyl bromide (7.05 g, 29.39 mmol) in dimethylformamide (20 mL) at 0° C. was added 60% sodium hydride (1.176 g, 29.39 mmol). After stirring at ambient temperature for 16 h, the reaction was partitioned between ethyl acetate and water. The organic layer was washed with aqueous sodium chloride and dried (MgSO4). Purification by flash column chromatography (silica gel, hexane/ethyl acetate) yielded an off-white solid (7.38 g, 89%). MS(ES) m/e 281.0 [M+H]+.

Provenance & Evidence