2-Cyclohexen-1-one → 3-Oxocyclohexane-1-carbonitrile

HRID 1819393Notes

Reaction equation

HRID 1819393 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[Al]([C:13]#[N:14])(CC)CC>C1(C)C=CC=CC=1>[O:7]=[C:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:13]#[N:14])[CH2:2]1

Participants

4

Reactant 2

HCID 135942-Cyclohexen-1-oneHCID 16683962(cyano-C)diethylaluminium

Product 1

HCID 128412163-Oxocyclohexane-1-carbonitrileYield 22%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-15 °C

Procedure

To a solution of 2-cyclohexen-1-one (6 mL, 62 mmol) in hexanes (100 mL) was added 1M Et2AlCN (160 mL) in toluene with cooling at −15° C. After stirring for 30 min, the reaction mixture was poured into an ice-cold 2M HCl solution and extracted with CH2Cl2. The extracts were washed with cold 2M NaOH and water, dried and concentrated in vacuo. Distillation of the product yielded 1.7 g (22%) of 3-oxo-cyclohexanecarbonitrile, b.p. 145-146° C. (16 mmHg).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe extracts were washed with cold 2M NaOH and water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. distillationDistillation of the product

Sources & evidence

ORD record
ord-1d969ad429e04251a7c00a8cac08291a
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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