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

HRID 989530Notes

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-tetramethyl-pieridin-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-12c9a5c477ac4d29a6635620a9c01d17
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06638997B2

Reaction notes

Loading…