Hydrogen Peroxide → 1-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-ol

HRID 133661

Reaktionsgleichung

Reaktionsgleichung von HRID 133661
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]1([CH3:12])[CH3:11].S(=O)(=O)(O)O.O.OO.[CH2:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>[Cu].C(#N)C>[CH:21]1([O:1][N:2]2[C:7]([CH3:8])([CH3:9])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]2([CH3:12])[CH3:11])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Komponenten

8

Edukt 5

HCID 784Hydrogen PeroxideHCID 962WaterHCID 1118Sulfuric Acid2×HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 8078Cyclohexane

Produkt 1

HCID 113228111-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-olAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Copper powder (0.060 g, 0.944 mmol) is added to a mixture of 5.00 g (29.0 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidin-4-ol, 44 ml of acetonitrile, and 30 ml of cyclohexane that has been heated to 40 degrees. A portion of a solution of 0.457 g of concentrated sulfuric acid in 3 mol of water is carefully added to the reaction mixture after the mixture is brought to reflux. To the refluxing reaction mixture is added dropwise over 2.5 hours a solution of 7.32 g (108 mmol) of 50% aqueous hydrogen peroxide. The remainder of the sulfuric acid solution is carefully added in portions to the reaction mixture during the first 15 minutes of the peroxide addition. After work up and purification according to the procedure of Example 54, the yield of the title compound is 5.22 g (70% yield), GC assay 94%.

Aufarbeitung

  1. temperaturehas been heated to 40 degrees
  2. temperatureto reflux
  3. customTo the refluxing reaction mixture
  4. customAfter work up and purification

Quellen und Nachweise

ORD-Eintrag
ord-80978fdb37144aa891b7f4777b60ed4c
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390904B2

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