Water → HCID 68601983, compound

Participants

Reaction Steps

2.75 g (68.4 mmol) of 60% sodium hydride is added in portions to a solution at 0° C. of 11 g (57 mmol) of (3-chloro-4-hydroxy-phenyl)-methyl acetate diluted in 60 ml of tetrahydrofuran and 60 ml of dimethylformamide. The reaction mixture is stirred at room temperature for 45 minutes and then 7.2 ml (62.7 mmol) of 2-methoxyethoxymethyl chloride is added dropwise. The reaction mixture is stirred at room temperature for 2 hours 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. 10.6 g (66%) of [3-chloro-4-(2-methoxy-ethoxymethoxy)-phenyl]-methyl acetate is obtained in the form of a colorless oil.

Provenance & Evidence