Hydrochloric Acid → 3-Cyclobutyl-2-hydroxybenzaldehyde

Participants

Reaction Steps

1-cyclobutyl-2-methoxymethoxybenzene (1.18 g) was dissolved in tetrahydrofuran (11 mL), and a 1.01M s-butyllithium-cyclohexane solution (8.7 mL) was added to the solution at −60° C. over 15 minutes under an argon gas flow, and then the mixture was stirred for 2 hours. N,N-dimethylformamide (0.90 mL) was added and the mixture was stirred at the same temperature for 2 hours. 4N hydrochloric acid (15 mL) was added at room temperature, and then the mixture was stirred at 60° C. for 20 hours. The solvent was distilled off under reduced pressure and water was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1) to obtain the title compound (0.95 g) as a colorless oily substance.

Provenance & Evidence