Di-tert-butyl peroxide → HCID 15169991, compound

HRID 1975574Notes

Reaction equation

HRID 1975574 reaction equation
[C:1]([O:9][CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[N:13]([OH:18])[C:12]([CH3:20])([CH3:19])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OOC(C)(C)C)(C)(C)C.[CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]=1>>[C:1]([O:9][CH:10]1[CH2:11][C:12]([CH3:20])([CH3:19])[N:13]([O:18][CH:36]2[CH2:35][CH2:34][CH2:33][CH:32]=[CH:31]2)[C:14]([CH3:16])([CH3:17])[CH2:15]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8033Di-tert-butyl peroxideHCID 8079CyclohexeneHCID 6881781-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 15169991HCID 15169991, compoundYield 81%

Procedure

A solution of 33.6 grams (122 mmol) of 4-benzoyloxy-1-oxyl-2,2,6,6-tetramethylpiperidine, 23.0 grams (157 mmol) of di-tert-butyl peroxide, and 70 ml of cyclohexene is heated in a Fischer-Porter pressure bottle at 138° C. for 6.5 hours. The reaction mixture is purified by flash chromatography on silica gel (200:1 heptane:ethyl acetate) to afford 35.1 grams (81% yield) of the title compound as a colorless oil.

Workup

  1. customThe reaction mixture is purified by flash chromatography on silica gel (200:1 heptane:ethyl acetate)

Sources & evidence

ORD record
ord-967baed66aa44628b837574e544d5093
Source dataset
uspto-grants-1994_02
Patent number
US05286865

Reaction notes

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