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tert-Butyl hydroperoxide → HCID 53631979, Verbindung

HRID 1590935
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1590935
[C:1]([O:22][CH:23]1[CH2:28][C:27]([CH3:30])([CH3:29])[NH:26][C:25]([CH3:32])([CH3:31])[CH2:24]1)(=[O:21])[C:2]1[C:3](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:4]([O:6][CH:7]1[CH2:12][C:11]([CH3:14])([CH3:13])[NH:10][C:9]([CH3:16])([CH3:15])[CH2:8]1)=[O:5].[C:33]([O:37]O)([CH3:36])([CH3:35])C>[Mo](=O)(=O)=O.C1CCCCC1>[C:4]([O:6][CH:7]1[CH2:8][C:9]([CH3:16])([CH3:15])[N:10]([O:37][CH:33]2[CH2:36][CH2:17][CH2:3][CH2:4][CH2:35]2)[C:11]([CH3:13])([CH3:14])[CH2:12]1)(=[O:5])[C:3]1[C:2](=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:1]([O:22][CH:23]1[CH2:24][C:25]([CH3:32])([CH3:31])[N:26]([O:37][CH:33]2[CH2:36][CH2:20][CH2:2][CH2:1][CH2:35]2)[C:27]([CH3:30])([CH3:29])[CH2:28]1)=[O:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 6410tert-Butyl hydroperoxide3×HCID 1513129Bis(2,2,6,6-tetramethyl-4-piperidinyl) phthalate

Produkt 1

HCID 53631979HCID 53631979, VerbindungAusbeute 143,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14802Molybdenum trioxideKatalysatorHCID 8078CyclohexaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 30.0 g (67.5 mmol) of di-(2,2,6,6-tetramethyl-piperidin-4-yl) phthalate, 27.5 g (214 mmol) of 70% aqueous t-butyl hydroperoxide, 2.0 g of molybdenum trioxide, and 200 ml of cyclohexane is heated to reflux. Water is collected in a Dean-Stark trap. After 75 min., the reaction mixture becomes red. Another portion of t-butyl hydroperoxide (42.5 g, 70%, 330 mmol) is added over 30 minutes. After the additional water is collected, the reaction mixture is transferred to a Fischer-Porter bottle and heated at 140° C. for 4.5 hours. The nearly colorless reaction mixture is treated with 6.9 g (90%, 69 mmol) of t-butyl hydroperoxide and heated at 140° C. for 90 minutes to remove the last traces of pink color. The reaction mixture is cooled, filtered, and stirred with a solution of 43 g of sodium sulfite in 530 ml of water for 2 hours. Dichloromethane (600 ml) is added, and the organic layer is separated, dried over magnesium sulfate, and concentrated to obtain a crude solid. Purification (Waters Prep. 500A HPLC, 25:1 heptane:ethyl acetate) affords 31.0 g (72% yield) of a white solid, m.p. 149°-51° C.

Aufarbeitung

  1. temperatureis heated to reflux
  2. customWater is collected in a Dean-Stark trap
  3. customAfter the additional water is collected
  4. temperatureheated at 140° C. for 90 minutes
  5. customto remove the last traces of pink color
  6. temperatureThe reaction mixture is cooled
  7. filtrationfiltered
  8. additionDichloromethane (600 ml) is added
  9. customthe organic layer is separated
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated
  12. customto obtain a crude solid
  13. customPurification (Waters Prep. 500A HPLC, 25:1 heptane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4fc763e57fd743adad48425debc9828b
Quelldatensatz
uspto-grants-1993_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05204473

Notizen zur Reaktion

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