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4-AcNH-TEMPO-CATALYZED OXIDATION OF ALDOSES TO ALDARIC ACIDS USING CHLORINE OR BROMINE AS TERMINAL OXIDANTS

The 4-AcNH-TEMPO-catalyzed oxidation of d-glucose to d-glucaric acid using elemental chlorine or bromine as the terminal oxidant is reported. The pH and temperature of the reactions were closely controlled to be between 0–5°C and pH 11.5, respectively. Spectroscopically (1H NMR) determined yields of glucarate were greater than 90%; yields of crystalline monopotassium d-glucarate (or disodium d-glucarate), isolated and purified by precipitation, were between 70 and 85%. Oxidations of mannose to mannaric acid and galactose to mucic acid were also demonstrated.