Adipic Acid → Cyclohexanone

HRID 1602070Notes

Reaction equation

HRID 1602070 reaction equation
C(#N)C1C=CC=CC=1.ON1C(=O)C2=CC=CC=C2C1=O.[C:21]([OH:30])(=O)[CH2:22][CH2:23][CH2:24][CH2:25][C:26](O)=O>C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C.C1CCCCC1>[C:21]1(=[O:30])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1.[CH:21]1([OH:30])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

7

Reactant 3

HCID 196Adipic AcidHCID 7505BenzonitrileHCID 10665N-Hydroxyphthalimide

Product 2

HCID 7966CyclohexanolYield 0.9%HCID 7967CyclohexanoneYield 11%

Reagents, catalysts & solvents 2

HCID 168478Rhodium acetateCatalystHCID 8078CyclohexaneSolvent2×

Procedure

To 10 ml of benzonitrile were added 10 mmol of cyclohexane, 1 mmol of N-hydroxyphthalimide, 0.01 mmol of rhodium acetate [Rh(OAc)2 ]2, and 0.1 mmol of acetylacetonatocobalt Co(AA)3 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 11%), cyclohexanol (yield 0.9%) and adipic acid (trace amount) with a conversion of 16%.

Sources & evidence

ORD record
ord-017692f798034fa48914963ddc0a111b
Source dataset
uspto-grants-1999_11
Patent number
US05981420

Reaction notes

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