Hydrogen Peroxide → 1-(2-Hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-one

HRID 1276649Notes

Reaction equation

HRID 1276649 reaction equation
OO.[OH:3][N:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][C:7](=[O:12])[CH2:6][C:5]1([CH3:14])[CH3:13].[C:15]([OH:19])([CH3:18])([CH3:17])[CH3:16]>>[OH:19][C:15]([CH3:18])([CH3:17])[CH2:16][O:3][N:4]1[C:9]([CH3:10])([CH3:11])[CH2:8][C:7](=[O:12])[CH2:6][C:5]1([CH3:14])[CH3:13]

Participants

4

Reactant 3

HCID 784Hydrogen PeroxideHCID 6386tert-Butanol2×HCID 986421-Hydroxy-2,2,6,6-tetramethyl-4-oxopiperidine

Product 1

HCID 218850571-(2-Hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-oneYield 2.5%

Conditions

Temperature
60 °C

Procedure

A solution of 1.0 g (15 mmol) of 50% aqueous hydrogen peroxide in 5 mL of tert-butyl alcohol is added over 30 minutes at 60° C. to a mixture of 0.5 g (2.9 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidin-4-one, 0.1 g (0.16 mmol) of N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(II) chloride (Jacobsen's catalyst), and 10 mL of tert-butyl alcohol. The reaction is stirred overnight at 60° C. Gas chromatography shows 2.5% of the title compound is present in the reaction mixture.

Sources & evidence

ORD record
ord-80e3ab36d18e4bdd8ce474e865abce10
Source dataset
uspto-grants-2000_12
Patent number
US06166212

Reaction notes

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