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

HRID 1936503Notes

Reaction equation

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

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-tetramethylpieridin-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-6701e5093fff484b99bcc0393e4c64e7
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06388072B2

Reaction notes

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