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

HRID 1276634Notes

Reaction equation

HRID 1276634 reaction equation
OO.C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.[OH: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.N=O.[C:37]([OH:41])([CH3:40])([CH3:39])[CH3:38]>O>[OH:23][CH:24]1[CH2:29][C:28]([CH3:30])([CH3:31])[N:27]([O:32][CH2:38][C:37]([OH:41])([CH3:40])[CH3:39])[C:26]([CH3:34])([CH3:33])[CH2:25]1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 945NitroxylHCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 6049Ethylenediaminetetraacetic AcidHCID 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 32.3 g (475 mmol) of 50% aqueous hydrogen peroxide mixed with 35 mL of tert-butyl alcohol is added over six hours at 45-50° C. to a mixture prepared by adding sequentially 0.362 g (1.2 mmol) of ethylenediaminetetraacetic acid, 55 mL of tert-butyl alcohol and 17.2 g (100 mmol) of 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine to a solution of 0.80 g (4 mmol) of ferrous chloride dissolved in 5 mL of water. Analysis by gas chromatography shows 15% starting nitroxyl compound remains at the end of the peroxide addition. The reaction mixture is stirred for one hour at 45-50° C. and then for 72 hours at 25° C. to complete the reaction. Analysis by gas chromatography shows the reaction mixture contains a ratio of 7 parts of the title compound to 1 part of 1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-one.

Workup

  1. additionis added over six hours at 45-50° C. to a mixture
  2. customprepared
  3. waitfor 72 hours at 25° C. to complete
  4. customthe reaction

Sources & evidence

ORD record
ord-8c3c64847c144c8289006a2aba2d2d1b
Source dataset
uspto-grants-2000_12
Patent number
US06166212

Reaction notes

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