Hydrogen Peroxide → 1-(2-Hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-one

HRID 843467

Reaction equation

OO.[OH:3][N:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][C:7](=[O:12])[CH2:6][C:5]1([CH3:14])[CH3:13].S([O-])([O-])=O.[Na+].[Na+].[C:21]([OH:25])([CH3:24])([CH3:23])[CH3:22]>>[OH:25][C:21]([CH3:24])([CH3:23])[CH2:22][O:3][N:4]1[C:9]([CH3:10])([CH3:11])[CH2:8][C:7](=[O:12])[CH2:6][C:5]1([CH3:14])[CH3:13]

Participants

Reactant 4

HCID 784Hydrogen Peroxide

HCID 6386tert-Butanol

HCID 24437Sodium Sulfite

HCID 986421-Hydroxy-2,2,6,6-tetramethyl-4-oxopiperidine

Product 1

HCID 218850571-(2-Hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-one

Procedure

Aqueous hydrogen peroxide is added to a mixture of 1-oxyl-2,2,6,6-tetramethylpiperidin-4-one and ferrous chloride in tert-butyl alcohol at 30-60° C. Excess peroxide is decomposed with aqueous sodium sulfite. The organic layer is concentrated and the residue is purified by flash chromatography to afford the desired 1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-piperidin-4-one.

Workup

concentrationThe organic layer is concentrated
customthe residue is purified by flash chromatography

Sources & evidence

ORD record: ord-8fc3491a2e5a4c1cafac998c1e415ecb
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376584B1

Linked notes

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