tert-Butyl hydroperoxide → 2,2,6,6-Tetramethyl-1-(1-phenylethoxy)piperidin-4-one

HRID 1493399Notes

Reaction equation

HRID 1493399 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][C:5](=[O:10])[CH2:4][C:3]1([CH3:12])[CH3:11].C(OO)(C)(C)C.[CH2:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:20]>[Mo](=O)(=O)=O>[CH3:20][CH:19]([O:1][N:2]1[C:7]([CH3:8])([CH3:9])[CH2:6][C:5](=[O:10])[CH2:4][C:3]1([CH3:12])[CH3:11])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 7500EthylbenzeneHCID 986421-Hydroxy-2,2,6,6-tetramethyl-4-oxopiperidine

Product 1

HCID 179683592,2,6,6-Tetramethyl-1-(1-phenylethoxy)piperidin-4-oneYield 67%

Reagents, catalysts & solvents 1

HCID 14802Molybdenum trioxideCatalyst

Procedure

A mixture of 40.0 grams (235 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidin-4-one, 60.5 grams (470 mmol) of 70% aqueous tert-butyl hydroperoxide, 3.0 grams of molybdenum trioxide, and 200 ml of ethylbenzene is heated at reflux for four hours. Water is collected in a Dean-Stark trap. Solids are removed by filtration, and the filtrate is concentrated under reduced pressure. Kugelrohr distillation of the crude product, followed by recrystallization from methanol, affords 42.8 grams (67% yield) of the title compound as a white solid melting at 77-80° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for four hours
  3. customWater is collected in a Dean-Stark trap
  4. customSolids are removed by filtration
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. distillationKugelrohr distillation of the crude product
  7. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-80fa3fae171f4d4dacc5aef797c84a0e
Source dataset
uspto-grants-1991_06
Patent number
US05021481

Reaction notes

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