Di-tert-butyl peroxide → 4-Benzoyloxy-1-methoxy-2,2,6,6-tetramethylpiperidine

HRID 1975550Notes

Reaction equation

HRID 1975550 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:21](OOC(C)(C)C)(C)(C)C>ClC1C=CC=CC=1>[C:1]([O:9][CH:10]1[CH2:11][C:12]([CH3:20])([CH3:19])[N:13]([O:18][CH3:21])[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 2

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

Product 1

HCID 8525384-Benzoyloxy-1-methoxy-2,2,6,6-tetramethylpiperidineYield 51.5%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 20.0 grams (72 mmol) of 4-benzoyloxy-1-oxyl-2,2,6,6-tetramethylpiperidine, 10.5 grams (72 mmol) of di-tert-butyl peroxide, and 30 ml of chlorobenzene is heated for six hours in a Fischer-Porter pressure bottle (nitrogen atmosphere, bath temperature 145°-150° C.). The crude reaction product is purified by flash chromatography (silica gel; 50:1 heptane:ethyl acetate) and then recrystallized from methanol to afford 10.8 grams (51% yield) of the title compound, a white solid melting at 67°-68° C.

Workup

  1. customThe crude reaction product
  2. customis purified by flash chromatography (silica gel; 50:1 heptane:ethyl acetate)
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-d205b67614c44c5fbc3d8e3aed633109
Source dataset
uspto-grants-1994_02
Patent number
US05286865

Reaction notes

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