4-Hydroxybenzaldehyde → 4-(Methoxymethoxy)benzaldehyde

Participants

Reaction Steps

4-Hydroxybenzaldehyde (500 mg, 4.09 mmol) and diisopropylethylamine (2.85 mL, 16.4 mmol) were dissolved in dichloromethane (10 mL). To this, chloromethyl methyl ether (614 μL, 8.09 mmol) was added under a nitrogen atmosphere at 0° C. and the mixture was stirred at room temperature for 8 hours. Then, water was added to the reaction mixture, and extraction with chloroform was performed, followed by drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3) to give 4-methoxymethoxybenzaldehyde (658 mg, yield: 97%).

Provenance & Evidence