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Octane → Tinuvin 123

HRID 133638
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 133638
[C:1]([O:25][CH:26]1[CH2:31][C:30]([CH3:33])([CH3:32])[N:29]([OH:34])[C:28]([CH3:36])([CH3:35])[CH2:27]1)(=[O:24])[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])[N:16]([OH:21])[C:15]([CH3:23])([CH3:22])[CH2:14]1)=[O:11].[CH3:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].OO.S([O-])([O-])=O.[Na+].[Na+]>O.C(O)(=O)C.C(#N)C>[C:1]([O:25][CH:26]1[CH2:27][C:28]([CH3:36])([CH3:35])[N:29]([O:34][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:30]([CH3:33])([CH3:32])[CH2:31]1)(=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH:13]1[CH2:14][C:15]([CH3:22])([CH3:23])[N:16]([O:21][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:17]([CH3:19])([CH3:20])[CH2:18]1)=[O:11]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 356OctaneHCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 11272241Bis(1-hydroxy-2,2,6,6-tetramethyl-4-piperidinyl)decandioate

Produkt 1

HCID 3592789Tinuvin 123Ausbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176
Acetic Acid
Lösungsmittel
3×
HCID 962WaterLösungsmittel3×
HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
76 °C

Versuchsvorschrift

A solution of 0.308 g (1.14 g) of ferric chloride hexahydrate and 0.225 g (3.75 mmol) of glacial acetic acid in 5 ml of water is added to a mixture of 10.00 g (19.6 mmol) of bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 94 ml of acetonitrile, and 64 ml of n-octane that is heated to 76° C. The reaction mixture is kept at the reflux temperature of 76° as a solution of 11.52 g (169 mmol) of 50% aqueous hydrogen peroxide is added dropwise over 3 hours. A solution of 0.106 g of ferric chloride hexahydrate and 0.102 g of glacial acetic acid in 1.6 g of water is added to the reaction mixture 1.75 hours after the peroxide addition is begun. A solution of 0.106 g of ferric chloride hexahydrate and 0.073 g of glacial acetic acid in 1.6 g of water is added to the reaction mixture 2.75 hours after the peroxide addition is begun. The reaction mixture is maintained at the reflux temperature for 1 hour after the peroxide is added. Excess peroxide is decomposed by stirring the reaction mixture with aqueous sodium sulfite solution. Solids are removed by filtration. The aqueous layer of the filtrate is extracted with ethyl acetate. The combined organic layers are concentrated, and the concentrate is purified twice by flash chromatography with a 100:7.5 mixture of heptane-ethyl acetate to afford 4.43 g (31% yield) of the title compound, a colorless liquid. NMR analysis shows a mixture of octyl regioisomers.

Aufarbeitung

  1. additionis added dropwise over 3 hours
  2. additionis added
  3. customSolids are removed by filtration
  4. extractionThe aqueous layer of the filtrate is extracted with ethyl acetate
  5. concentrationThe combined organic layers are concentrated
  6. customthe concentrate is purified twice by flash chromatography with a 100:7.5 mixture of heptane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2ea7aa7d72964983a1f9433f940eb17b
Quelldatensatz
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07390904B2

Notizen zur Reaktion

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