Potassium Permanganate → 4,6-Dimethylpicolinic acid

Temperature

2.5 °C

4,6-Dimethyl-2-pyridinemethanol (7.5 g, 29.2 mmol) was added to 100 mL of water and stirred at 0-5° C. A solution of 5.3 g (32.1 mmol) of potassium permanganate in 100 mL of water was added portion-wise over 30 min while maintaining the temperature at 5-10° C. This resulted in the formation of a black solid. The mixture was stirred at 5-10° C. for an additional 30 min and then allowed to stir at room temperature for 30 min. The mixture was filtered and the manganese dioxide washed with methanol. The methanol washings were combined with the water extracts and the solvent was removed. The resulting tan solid was redissolved in water and washed with chloroform. The water layer was separated and the water removed to yield 5.4 g of 4,6-dimethyl-2-pyridinecarboxylic acid. The product was characterized by HPLC/MS.

1. temperaturewhile maintaining the temperature at 5-10° C
2. customThis resulted in the formation of a black solid
3. stirringThe mixture was stirred at 5-10° C. for an additional 30 min
4. stirringto stir at room temperature for 30 min
5. filtrationThe mixture was filtered
6. washthe manganese dioxide washed with methanol
7. customthe solvent was removed
8. dissolutionThe resulting tan solid was redissolved in water
9. washwashed with chloroform
10. customThe water layer was separated
11. customthe water removed

ORD record

ord-4f5c271e02c24ab481582a6052898936

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359289B2