Sulfuric Acid → HCID 13537602, compound

Participants

Reaction Steps

To a mixture of 12.8 g of 2-[3-(2,4-dichlorobenzoyl)-isoxazol-5-yl]ethanol and a few crystals of tetra-n-butylammonium hydrogen sulfate in 1000 ml of CH2Cl2 was added 150 ml of 9M H2SO4. To this was added 13.2 g of pulverized K2Cr2O7 and the mixture was stirred at room temperature for 1 hour. The organic phase was separated from the aqueous phase and washed with water. The acid product was extracted from the organic phase using 40 ml of 4% NaHCO3. The alkaline solution was washed with CH2Cl2 several times, until all the neutral impurities were removed, and the solution was then acidified slowly with 5% HCl until all the acid precipitated. The solid was filtered, washed with water, and dried to yield 3.9 g of a powder. Recrystallization from 100 ml of 50% toluene/hexane gave 3.5 g (26%) of crystals, m.p. 108°-109° .

Provenance & Evidence