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Hydrochloric Acid → Lauryl 3-[N-(1-Octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N-hydroxyamino]propionate

HRID 741783
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 741783
[CH2:1]([O:9][N:10]1[C:15]([CH3:17])([CH3:16])[CH2:14][C:13](=[N:18][OH:19])[CH2:12][C:11]1([CH3:21])[CH3:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl.[H][H].[C:25]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])(=[O:28])[CH:26]=[CH2:27]>[Pt].CO>[CH2:1]([O:9][N:10]1[C:11]([CH3:20])([CH3:21])[CH2:12][CH:13]([N:18]([CH2:27][CH2:26][C:25]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:28])[OH:19])[CH2:14][C:15]1([CH3:17])[CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 75084Lauryl acrylateHCID 229026981-Octyloxy-2,2,6,6-tetramethylpiperidin-4-one oximeHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 22902716Lauryl 3-[N-(1-Octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N-hydroxyamino]propionateAusbeute 57,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 1-octyloxy-2,2,6,6-tetramethylpiperidin-4-one oxime (10.0 g, 35.4 mmol) (a mixture of octyloxy isomers) 5.5 ml of concentrated hydrochloric acid and 130 ml of methanol is subjected to 3 atmospheres of hydrogen over 5% platinum on carbon for 18 hours. The reaction mixture is filtered through celite and then concentrated. The residue is partitioned between ethyl acetate and aqueous potassium carbonate. The organic layer is washed with water and brine, dried over anhydrous sodium sulfate and finally concentrated to a total volume of about 150 ml. Lauryl acrylate (7.7 g, 32 mmol ) is added. After a two-hour reaction time, the reaction mixture is concentrated and the crude product purified by flash chromatography on silica gel (9:1, hexane:ethyl acetate) to yield 10.0 g (52% yield) of a clear oil.

Aufarbeitung

  1. filtrationThe reaction mixture is filtered through celite
  2. concentrationconcentrated
  3. customThe residue is partitioned between ethyl acetate and aqueous potassium carbonate
  4. washThe organic layer is washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationfinally concentrated to a total volume of about 150 ml
  7. customAfter a two-hour reaction time
  8. concentrationthe reaction mixture is concentrated
  9. customthe crude product purified by flash chromatography on silica gel (9:1, hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-6edf92e84dbe4363b2dee818ac08c813
Quelldatensatz
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05552464

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