Hydrochloric Acid → 4-Piperidinol, 1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-

HRID 1276651Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[N:5]([OH:10])[C:4]([CH3:12])([CH3:11])[CH2:3]1.Cl.[C:14]([OH:18])([CH3:17])([CH3:16])[CH3:15]>O>[OH:1][CH:2]1[CH2:7][C:6]([CH3:8])([CH3:9])[N:5]([O:10][CH2:15][C:14]([OH:18])([CH3:17])[CH3:16])[C:4]([CH3:12])([CH3:11])[CH2:3]1

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of 5.2 g (30 mmol) of 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine dissolved in 20 mL of water and a solution of 7.8 g (61 mmol) of 70% aqueous tert-butyl hydroxperoxide are added simultaneously over one hour at 35-50° C. to a mixture of 0.33 g (1.2 mmol) of ferric chloride hexahydrate, 8 mL of water, 0.2 mL of 37% hydrochloric acid, and 60 mL of tert-butyl alcohol. The reaction mixture is maintained at 45° C. for one hour after the addition and is then stirred at room temperature for three days. Gas chromatography shows 3% of the title compound is present in the reaction mixture.

Workup

additionafter the addition

Sources & evidence

ORD record: ord-90e7eed7049f43fc817225459aa7bda0
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166212

Reaction notes

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