Adipic Acid → Cyclohexanone

HRID 1602069Notes

Reaction equation

HRID 1602069 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>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

6

Reactant 3

HCID 196Adipic AcidHCID 7505BenzonitrileHCID 10665N-Hydroxyphthalimide

Product 2

HCID 7966CyclohexanolYield 0.8%HCID 7967CyclohexanoneYield 10%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent2×

Procedure

To 10 ml of benzonitrile were added 10 mmol of cyclohexane, 1 mmol of N-hydroxyphthalimide, 0.01 mmol of cobalt acetate Co(OAc)2, and 0.1 mmol of acetylacetonatochromium Cr(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 10%), cyclohexanol (yield 0.8%) and adipic acid (trace amount) with a conversion of 33%.

Sources & evidence

ORD record
ord-7b1c7b258c74409690236d81c2fa4fb0
Source dataset
uspto-grants-1999_11
Patent number
US05981420

Reaction notes

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