Hydrogen Peroxide → Bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl] Succinate

HRID 1356908Notes

Reaction equation

OO.[OH:3][N:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][CH:7]([O:12][C:13](=[O:30])[CH2:14][CH2:15][C:16]([O:18][CH:19]2[CH2:24][C:23]([CH3:26])([CH3:25])[N:22]([OH:27])[C:21]([CH3:29])([CH3:28])[CH2:20]2)=[O:17])[CH2:6][C:5]1([CH3:32])[CH3:31].S([O-])([O-])=O.[Na+].[Na+].[C:39]([OH:43])([CH3:42])([CH3:41])[CH3:40]>>[OH:43][C:39]([CH3:42])([CH3:41])[CH2:40][O:27][N:22]1[C:21]([CH3:29])([CH3:28])[CH2:20][CH:19]([O:18][C:16](=[O:17])[CH2:15][CH2:14][C:13]([O:12][CH:7]2[CH2:6][C:5]([CH3:32])([CH3:31])[N:4]([O:3][CH2:40][C:39]([OH:43])([CH3:42])[CH3:41])[C:9]([CH3:11])([CH3:10])[CH2:8]2)=[O:30])[CH2:24][C:23]1([CH3:26])[CH3:25]

Participants

Reactant 4

HCID 784Hydrogen Peroxide

HCID 6386tert-Butanol

HCID 24437Sodium Sulfite

HCID 326921Bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) butanedioate

Product 1

HCID 54162330Bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl] Succinate

Procedure

Aqueous hydrogen peroxide is added to a mixture of bis(1-oxyl-2,2,6,6-tetramethyl-pieridin-4-yl)succinate and ferrous chloride tetrahydrate in tert-butyl alcohol at 30-50° C. Excess peroxide is decomposed with aqeuous sodium sulfite solution. The organic layer is concentrated and the crude product is purified by flash chromatography on silica gel to afford the title compound.

Workup

concentrationThe organic layer is concentrated
customthe crude product is purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-1badbc53cc4f4be1b18e0a8a8b75cb79
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586507B2

Reaction notes

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