Benzonitrile → Cyclohexanone

HRID 1602068Notes

Reaction equation

HRID 1602068 reaction equation
C(#N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9]N1C(=O)C2=CC=CC=C2C1=O>C1CCCCC1>[C:2]1(=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH:2]1([OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 7505BenzonitrileHCID 10665N-Hydroxyphthalimide

Product 2

HCID 7966CyclohexanolYield 1%HCID 7967CyclohexanoneYield 10%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent2×

Procedure

To 20 ml of benzonitrile were added 10 mmol of cyclohexane, 1 mmol of N-hydroxyphthalimide, 0.01 mmol of cobalt acetate Co(OAc)2, and 0.05 mmol of acetylacetonatocobalt Co(AA)2 and the resultant mixture was stirred under an oxygen atmosphere at a temperature of 75° C. for 16 hours. The products in the reaction mixture were analyzed by gas chromatography, and, as a result, cyclohexane was converted into cyclohexanone (yield 10%) and cyclohexanol (yield 1%) with a conversion of 12%. Adipic acid was not detected. The selectivity of K/A oil was 93% based on the consumed cyclohexane.

Sources & evidence

ORD record
ord-65977e8ac92d4e15b1f64bae111a8cc9
Source dataset
uspto-grants-1999_11
Patent number
US05981420

Reaction notes

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