Sulfuric Acid → [3-(4-Chlorobenzoyl)isoxazol-5-yl]acetic acid

Participants

Reaction Steps

To a mixture of 8.8 g of 2-[3-(4-chlorobenzoyl)isoxazol-5-yl)ethanol, 850 ml of CH2Cl2, a few crystals of tetra-n-butylammonium hydrogen sulfate and 130 ml of 9M H2SO4 was added 10.3 g of pulverized K2Cr2O7. The resulting mixture was stirred at room temperature for 2 hours. After allowing the mixture to settle, it was decanted from the unreacted dichromate. The aqueous phase was extracted with CH2Cl2, and the organics were washed with water and brine, and dried over MgSO4. Concentration gave 5.1 g of a solid. Recrystallization from toluene gave 3.0 g (32%) of needles, m.p. 126°-128°.

Provenance & Evidence