Iodoethane → 4-Ethoxy-3-hydroxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

Commercially available 3,4-dihydroxy benzaldehyde (35.8 g, 259 mmol) and potassium carbonate (37.6 g, 272 mmol) were dissolved in N,N-dimethylformamide (150 mL), then commercially available iodoethane (22 mL, 275 mmol) was added under nitrogen atmosphere at 0° C., and then the mixture was stirred for 2 days. The solvent was evaporated under vacuum, the resultant was cooled to 0° C., and then 5 M hydrochloric acid, ethyl acetate, and water were added for partition. The aqueous layer was extracted with ethyl acetate, the combined organic layer was washed with water twice and then with a saturated saline solution, and the mixture was dried over anhydrous magnesium sulfate and then filtered. The solvent was evaporated, then dichloromethane was added, and then the precipitate was collected by filteration to obtain the title compound (25.8 g, 60%). The filtrate was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-4:1-1:1). The target fraction was concentrated under vacuum, then diethyl ether and dichloromethane were added to the residue, and the precipitate was collected by filteration to obtain the title compound (3.45 g, 8.0%).

Provenance & Evidence