Water → 2,2-Dimethyl-5-oxocyclohexane-1-carbonitrile

HRID 1269955Notes

Reaction equation

[Cl-].[NH4+:2].[C-:3]#N.[K+].[CH3:6][C:7]1([CH3:14])[CH2:12][CH2:11][C:10](=[O:13])[CH:9]=[CH:8]1.O>CN(C)C=O>[CH3:6][C:7]1([CH3:14])[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH:8]1[C:3]#[N:2]

Participants

Conditions

Temperature: 70 °C

Procedure

Under a nitrogen atmosphere, an aqueous solution (10 ml) of ammonium chloride (2.37 g, 0.0443 mol) and an aqueous solution (20 ml) of potassium cyanide (3.15 g, 0.0483 mol) were added dropwise to a solution of 4,4-dimethyl-2-cyclohexen-1-one (5.0 g, 0.0403 mol) in N,N-dimethylformamide (30 ml) at room temperature, and the resulting mixture was heated to 70° C. After 2 hours, the reaction solution was poured into water and extracted with diethyl ether and then dichloromethane. The organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 2,2-dimethyl-5-oxocyclohexanecarbonitrile (4.033 g, 66%).

Workup

extractionextracted with diethyl ether
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customThe organic layer dried
concentrationwas concentrated under reduced pressure
customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record: ord-6e0498a6aa8943698f2d73794c09e91e
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199147B2

Reaction notes

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