Water → HCID 86642400, compound

Participants

Reaction Steps

1.8 g (41.2 mmol) of 60% sodium hydride is added in portions to a solution at 0° C. of 5.7 g (37.5 mmol) of 4-hydroxy-2-methoxy-benzaldehyde diluted in 30 ml of tetrahydrofuran and 30 ml of dimethylformamide. The reaction mixture is stirred at room temperature for 30 minutes and then 4.7 ml (41.2 mmol) of 2-methoxyethoxymethyl chloride is added dropwise. The reaction mixture is stirred at room temperature for 45 minutes and then the reaction mixture is treated by adding water and extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated. The raw product is purified by silica column chromatography, eluted with a heptane/ethyl acetate mixture 70/30 to give 8.6 g (95%) of 2-methoxy-4-(2-methoxy-ethoxymethoxy)-benzaldehyde in the form of a colorless oil.

Provenance & Evidence