Hydrogen Peroxide → HCID 12084308, compound

HRID 1276647Notes

Reaction equation

OO.[C:3]([O:11][CH:12]1[CH2:17][C:16]([CH3:19])([CH3:18])[N:15]([OH:20])[C:14]([CH3:22])([CH3:21])[CH2:13]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:23]([OH:27])([CH3:26])([CH3:25])[CH3:24]>>[C:3]([O:11][CH:12]1[CH2:13][C:14]([CH3:22])([CH3:21])[N:15]([O:20][CH2:24][C:23]([OH:27])([CH3:26])[CH3:25])[C:16]([CH3:18])([CH3:19])[CH2:17]1)(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Reactant 3

HCID 784Hydrogen Peroxide

HCID 6386tert-Butanol2×

HCID 6881781-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 12084308HCID 12084308, compound

Conditions

Temperature: 40 °C

Procedure

A solution of 20.4 g (0.30 mol) of 50% aqueous hydrogen peroxide mixed with 25 mL of tert-butyl alcohol is added over three hours to a mixture of 27.6 g (0.10 mol) of 4-benzoyloxy-1-oxyl-2,2,6,6-tetramethylpiperidine, 7.13 g (0.036 mol) of ferrous choride tetrahydrate and 115 mL of tert-butyl alcohol at 40° C. The reaction temperature is maintained at 40° C. for twenty hours after the peroxide addition is complete. The crude reaction mixture is purified by flash chromatography on silica gel to afford 16.2 g of the title compound.

Workup

customThe crude reaction mixture
customis purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-7bfa71a77cee4840b51597ac1b917695
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166212

Reaction notes

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