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

HRID 844899Notes

Reaction equation

OO.[C:3]([O:23][CH:24]1[CH2:29][C:28]([CH3:31])([CH3:30])[N:27]([OH:32])[C:26]([CH3:34])([CH3:33])[CH2:25]1)(=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH:11]1[CH2:16][C:15]([CH3:18])([CH3:17])[N:14]([OH:19])[C:13]([CH3:21])([CH3:20])[CH2:12]1)=[O:9].S([O-])([O-])=O.[Na+].[Na+].[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>>[OH:45][C:41]([CH3:44])([CH3:43])[CH2:42][O:19][N:14]1[C:15]([CH3:18])([CH3:17])[CH2:16][CH:11]([O:10][C:8](=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][C:3]([O:23][CH:24]2[CH2:25][C:26]([CH3:34])([CH3:33])[N:27]([O:32][CH2:42][C:41]([OH:45])([CH3:44])[CH3:43])[C:28]([CH3:31])([CH3:30])[CH2:29]2)=[O:22])[CH2:12][C:13]1([CH3:21])[CH3:20]

Participants

Reactant 4

HCID 784Hydrogen Peroxide

HCID 6386tert-Butanol

HCID 24437Sodium Sulfite

HCID 57039687Bis(1-oxyl-2,2,6,6-tetramethyl-pieridin-4-yl)adipate

Product 1

HCID 54450908bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]Adipate

Procedure

Aqueous hydrogen peroxide is added to a mixture of bis(1-oxyl-2,2,6,6-tetramethylpieridin-4-yl) adipate and ferrous chloride tetrahydrate in tert-butyl alcohol at 30-50° C. Excess peroxide is decomposed with aqueous 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-282ae97521114378a96d42beb0cb3bb0
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380389B2

Reaction notes

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