Dimethyl Sulfoxide → 1-Methoxy-2,2,6,6-tetramethyl-piperidin-4-ol

HRID 1492700Notes

Reaction equation

HRID 1492700 reaction equation
OO.[OH:3][CH:4]1[CH2:9][C:8]([CH3:11])([CH3:10])[N:7]([OH:12])[C:6]([CH3:14])([CH3:13])[CH2:5]1.[CH3:15]S(C)=O.CCCCCCC.C(OCC)(=O)C>O>[CH3:15][O:12][N:7]1[C:8]([CH3:10])([CH3:11])[CH2:9][CH:4]([OH:3])[CH2:5][C:6]1([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 21899848Ethylacetate heptane

Product 1

HCID 109977701-Methoxy-2,2,6,6-tetramethyl-piperidin-4-olYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 17.9 g (64.4 mmol) of ferrous sulfate heptahydrate in 80 ml of water and a solution of 9.7 g (86 mmol) of 30% aqueous hydrogen peroxide are simultaneously added, under nitrogen, over a 90-minute interval to a mixture of 10.0 g (58.1 mmol) of 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine and 100 ml of dimethyl sulfoxide which is initially at 23° C. The temperature increases to 29° C. during the peroxide addition. After the addition is complete, the reaction mixture is stirred for two hours. The mixture is extracted with methylene chloride (200 ml, then 100 ml), and the crude product is purified by flash chromatography on silica gel (10:1 heptane/ethyl acetate, then 5:1 heptane/ethyl acetate) to afford 6.9 g (63% yield) of the title compound.

Workup

  1. customis initially at 23° C
  2. additionAfter the addition
  3. extractionThe mixture is extracted with methylene chloride (200 ml
  4. custom100 ml), and the crude product is purified by flash chromatography on silica gel (10:1 heptane/ethyl acetate

Sources & evidence

ORD record
ord-2ef98f562c17445ba94df7ac189bc654
Source dataset
uspto-grants-1994_12
Patent number
US05374729

Reaction notes

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