Water → HCID 17760218, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled solution (ice bath) of 10.8 g of methyl 4-acetamido-3-chloro-5-methylbenzoate in 73.8 ml of glacial acetic acid; and 73.8 ml of acetic anhydride were added dropwise 11 mL of concentrated sulfuric acid followed by the portion wise addition of 12.96 g (0.1295 mole) of chromium trioxide over a 25 minute period. The reaction mixture was stirred at 0° C. for 2.5 hours and then poured into a mixture of 612 g of ice and 162 ml of water. The resulting aqueous mixture was extracted with methylene chloride (4×250 ml). The combined organic layers were washed sequentially with water (3×250 ml), 5% aqueous sodium bicarbonate (2×250 ml) and then brine (1×250 ml) and dried over anhydrous magnesium sulfate. The solvent was removed in a rotary evaporator. The resulting residue was purified by chromatographic column (silica gel, ethyl acetate:hexane 30:70 followed by ethyl acetate:hexane 50:50), yielding 2.5 g methyl 4-acetamido-3-chloro-5-formylbenzoate.

Provenance & Evidence