tert-Butyl hydroperoxide → Tinuvin 123

HRID 1650044

Reaktionsgleichung

Reaktionsgleichung von HRID 1650044
[C:1]([O:24][CH:25]1[CH2:30][C:29]([CH3:32])([CH3:31])[NH:28][C:27]([CH3:34])([CH3:33])[CH2:26]1)(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH:13]1[CH2:18][C:17]([CH3:20])([CH3:19])[NH:16][C:15]([CH3:22])([CH3:21])[CH2:14]1)=[O:11].[C:35]([O:39]O)([CH3:38])(C)C>[O-2].[Cr+6].[O-2].[O-2].CCCCCCCC>[C:1]([O:24][CH:25]1[CH2:30][C:29]([CH3:32])([CH3:31])[N:28]([O:39][CH2:35][CH2:38][CH2:21][CH2:15][CH2:14][CH2:13][CH2:18][CH3:17])[C:27]([CH3:34])([CH3:33])[CH2:26]1)(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH:13]1[CH2:18][C:17]([CH3:19])([CH3:20])[N:16]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH3:3])[C:15]([CH3:21])([CH3:22])[CH2:14]1)=[O:11]

Komponenten

5

Edukt 2

HCID 6410tert-Butyl hydroperoxideHCID 164282Tinuvin 770

Produkt 1

HCID 3592789Tinuvin 123Ausbeute 133 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10219390chromium (VI) trioxideKatalysatorHCID 356OctaneLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

A mixture of 15.0 g (31.2 mmol) of di-(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 0.2 g of chromium (VI) oxide, and 120 ml of n-octane is heated to 115° C. To the above mixture is added 28.5 g (221 mmol) of 70% aqueous tert-butyl hydroperoxide over a 90-minute interval while the reaction mixture is heated at reflux. Water is collected in a Dean-Stark trap. The red mixture is heated at reflux for 3.25 hours after the addition is complete in order to discharge the color. The reaction mixture is passed through 150 g of silica gel with 2:1 heptane:ethyl acetate as the eluent. The organic solution is evaporated to obtain a yellow liquid which is purified (Waters 500A HPLC; silica gel; 20:1 hexane:ethyl acetate) to afford 15.3 g (67% yield) of the title compound. The product has the same LC retention time as the compound prepared in Example 31.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux
  3. customWater is collected in a Dean-Stark trap
  4. temperatureThe red mixture is heated
  5. temperatureat reflux for 3.25 hours
  6. additionafter the addition
  7. customThe organic solution is evaporated
  8. customto obtain a yellow liquid which
  9. customis purified (Waters 500A HPLC; silica gel; 20:1 hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-34283d4289e24c63af56dbfb8ac22797
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04921962

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