Hydrogen Peroxide → 4-Piperidinol, 1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-

HRID 1276639Notes

Reaction equation

HRID 1276639 reaction equation
OO.[C:3]([OH:7])([CH3:6])([CH3:5])[CH3:4].[OH: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.N=O>O>[OH:8][CH:9]1[CH2:14][C:13]([CH3:15])([CH3:16])[N:12]([O:17][CH2:4][C:3]([OH:7])([CH3:6])[CH3:5])[C:11]([CH3:19])([CH3:18])[CH2:10]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 945NitroxylHCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 6386tert-Butanol2×

Product 1

HCID 68508284-Piperidinol, 1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
47.5 °C

Procedure

A solution of 9.4 g (140 mmol) of 50% aqueous hydrogen peroxide mixed with 20 mL of tert-butyl alcohol is added over four hours at 45-50° C. to a mixture of 3.44 g (20.0 mmol) of 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine, 0.125 g (0.77 mmol) of anhydrous ferric chloride, 30 mL of tert-butyl alcohol and 10 mL of water. The temperature is then maintained at 45-50° C. for 19 hours. Analysis by gas chromatography shows less than 1% of the starting nitroxyl compound is present.

Sources & evidence

ORD record
ord-0a44c5f691624875a948357268a7efcb
Source dataset
uspto-grants-2000_12
Patent number
US06166212

Reaction notes

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