Hydrogen Peroxide → 4-(tert-Butyl)pyridine 1-Oxide

To a stirred solution of 4-tert-butylpyridine (19.0 g) in acetic acid (90 ml) was added dropwise 50% of hydrogen peroxide aqueous solution (20 ml) at room temperature and stirred for 30 minutes under the same condition. The mixture was stirred for 3 hours at ca.80° C. After cooling to room temperature, to the mixture was added dropwise another 20 ml of 50% hydrogen peroxide aqueous solution and stirred for 30 minutes. The mixture was stirred for 3 hours at ca. 80° C. After cooling to room temperature, the mixture was concentrated in vacuo. The residue was taken up with chloroform, and washed with water (50 ml), saturated sodium carbonate aqueous solution (50 ml) and water (50 ml). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give 4-tert-butyl-1-oxypyridine, which was crystallized by isopropyl ether as a colorless powder (19.1 g).

1. stirringThe mixture was stirred for 3 hours at ca
2. custom80° C
3. stirringstirred for 30 minutes
4. stirringThe mixture was stirred for 3 hours at ca. 80° C
5. temperatureAfter cooling to room temperature
6. concentrationthe mixture was concentrated in vacuo
7. washwashed with water (50 ml), saturated sodium carbonate aqueous solution (50 ml) and water (50 ml)
8. dry with materialThe organic layer was dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-113249283e7c49fd9ce33c55b3d2434b

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05763437