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

HRID 985873Notes

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]>>[C:3]([O:21][CH:22]1[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]1)(=[O:20])[CH2:4][CH2:5][C:6]([O:8][CH:9]1[CH2:14][C:13]([CH3:16])([CH3:15])[N:12]([O:17][CH2:40][C:39]([OH:43])([CH3:42])[CH3:41])[C:11]([CH3:19])([CH3:18])[CH2:10]1)=[O:7]

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-65ebc1b14af843a1844b205c8ad6ea96
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872832B2

Reaction notes

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