Methane → 1-(4-Hydroxyphenyl)-4,4-dimethylpiperidine-2,6-dione

HRID 1179656Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1179656
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][C:10]1([CH3:18])[CH2:16][C:15](=O)[O:14][C:12](=[O:13])[CH2:11]1.C.O.C(O)C>C(O)C>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([N:1]2[C:12](=[O:13])[CH2:11][C:10]([CH3:18])([CH3:9])[CH2:16][C:15]2=[O:14])=[CH:3][CH:4]=1

Komponenten

6

Edukt 4

HCID 297MethaneHCID 4034-AminophenolHCID 778133,3-Dimethylglutaric anhydrideHCID 19096565Water ethanol

Produkt 1

HCID 220477421-(4-Hydroxyphenyl)-4,4-dimethylpiperidine-2,6-dioneAusbeute 50,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
165 °C

Versuchsvorschrift

A mixture of 4-aminophenol (3.27 g, 30.0 mmol) and 3,3-dimethylglutaric anhydride (4.26 g, 30.0 mmol) was heated in a round bottom flask at 165° C. for 1 h, followed by heating at 180° C. for 7 h. After cooling to room temperature the solid material was dissolved in hot ethanol, activated charcoal was added and the solution was heated at reflux for 1 h. The solid material was removed by hot filtration. The solvent was evaporated and the residue was crystallised from water/ethanol yielding the title compound (3.51 g, 50% yield, pink solid).

Aufarbeitung

  1. temperatureby heating at 180° C. for 7 h
  2. temperatureAfter cooling to room temperature the solid material
  3. temperaturethe solution was heated
  4. temperatureat reflux for 1 h
  5. customThe solid material was removed by hot filtration
  6. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-181426e626a44d35b8dc19f3373fdcc6
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279470B2

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