Ethanol → 2,2-Dimethylcyclopentanone

HRID 359346

Reaction equation

HRID 359346 reaction equation
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

Participants

6

Reactant 3

HCID 702EthanolHCID 73974-Toluenesulfonyl chlorideHCID 443297Hydroxyamine hydrochloride

Product 2

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

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

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.

Workup

  1. temperatureHeating

Sources & evidence

ORD record
ord-a010d9c3c9ea409e9b454f9466a6ce01
Source dataset
uspto-grants-1991_03
Patent number
US05001113

Linked notes

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