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

Temperature

0 °C

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) under 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 magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-4/1) to give the title compound (5.22 g, yield 60%) as colorless crystals.

1. stirringthe mixture was stirred at the same temperature for 3 hr
2. customAfter completion of the reaction
3. extractionthe mixture was extracted with ethyl acetate
4. dry with materialThe organic layer was dried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-4/1)

ORD record

ord-016361b8c38d4b3d9e07bad1a0b7374c

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07786165B2