Hydrochloric Acid → 94283-73-5

Participants

Reaction Conditions

Reaction Steps

Commercially available 3,4-dihydroxybenzaldehyde (5 g, 36.2 mmol) and potassium carbonate (5.15 g, 37.3 mmol) were dissolved in N,N-dimethylformamide (20 mL), then 2-bromopropane (3.5 mL, 37.3 mmol) was added under nitrogen atmosphere at room temperature, and the mixture was heated and stirred at 40° C. for 2.5 hours. The reaction mixture was cooled to 0° C., and then 2 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 and a saturated saline solution, and the resultant was dried over anhydrous magnesium sulfate and then filtered. The solvent was evaporated, dichloromethane was added to the residue, the precipitate was separated by filtration, and the filtrate was concentrated under vacuum. The residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=19:1-13:7) and then the target fraction was concentrated under vacuum to obtain the title compound (1.84 g, 28%).

Provenance & Evidence