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

HRID 2229954Notes

Reaction equation

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

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 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-f09c835cc6f94705932e2f2c140b2b58
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06420463B1

Reaction notes

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