Methoxyacetyl chloride → 3-(Chloromethyl)-4-isobutoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-isobutoxybenzaldehyde (6.9 g, 38.7 mmol), aluminum chloride (12.9 g, 96.8 mmol) and nitromethane (39 mL) was added methoxyacetyl chloride (4.1 mL, 44.5 mmol), with stirring at 0° C., and the mixture was stirred at the same temperature for 3 hr. After completion of the reaction, the reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=4/1) to give the title compound (5.22 g, yield 60%) as colorless crystals. 1H NMR (CDCl3) δ: 1.08 (6H, d, J=6.9 Hz), 2.19 (1H, m), 3.89 (2H, d, J=6.0 Hz), 4.68 (2H, s), 6.98 (1H, d, J=8.4 Hz), 7.84 (1H, dd, J=2.1, 8.4 Hz), 7.91 (1H, d, J=2.1 Hz), 9.89 (1H, s).

Provenance & Evidence