Ethanol → 2,2-Dimethylcyclopentanone

HRID 359346

Reaktionsgleichung

Reaktionsgleichung von HRID 359346
Cl.[NH2:2]O.[C:4]1([CH3:14])[CH:9]=[CH:8][C:7](S(Cl)(=O)=O)=[CH:6][CH:5]=1.[CH3:15][CH2:16][OH:17]>CN(C1C=CN=CC=1)C>[CH3:14][C:4]1([CH3:5])[CH2:9][CH2:8][CH2:7][C:6]1=[O:17].[CH3:5][C:4]1([CH3:14])[NH:2][C:16](=[O:17])[CH2:15][CH2:8][CH2:9]1

Komponenten

6

Edukt 3

HCID 702EthanolHCID 73974-Toluenesulfonyl chlorideHCID 443297Hydroxyamine hydrochloride

Produkt 2

HCID 1382862,2-DimethylcyclopentanoneHCID 17144076,6-Dimethylpiperidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Versuchsvorschrift

The oxime of 2,2 dimethylcyclopentanone is prepared by reaction of the ketone with hydroxylamine hydrochloride in EtOH, and treated with p-toluenesulfonyl chloride and DMAP. Heating then effects Beckmann rearrangement to give 6,6-dimethyl-2-piperidinone which is deprotonated with NaH in DMF solution. Reaction with n-butyl iodide then gives the title compound.

Aufarbeitung

  1. temperatureHeating

Quellen und Nachweise

ORD-Eintrag
ord-a010d9c3c9ea409e9b454f9466a6ce01
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US05001113

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