Permanganate → 5-Bromobenzo(1,3)dioxole-4-carboxylic acid

Participants

Reaction Steps

Potassium permanganate (1.03 g, 6.55 mmol) was dissolved in water (25 mL). 5-Bromo-1,3-benzodioxole-4-carboxaldehyde (0.60 g, 2.62 mmol) was dissolved in acetone (25 mL) and slowly added to the permanganate solution and the reaction mixture was stirred at ambient temperature for 24 h at which time TLC analysis indicated the reaction complete. The reaction mixture was quenched with 5% sodium sulfite (100 mL). Concentrated HCl (10 mL) was added and the mixture turned a pale yellow color. The solution was extracted with ethyl acetate and the organic layers were dried with magnesium sulfate and concentrated by rotary evaporation to afford 0.34 g of product (1.39 mmol, 53% yield) as an off-white solid.

Provenance & Evidence