Acetic Acid → 4-Cyanobenzoic acid

HRID 1182335Notes

Reaction equation

HRID 1182335 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([C:7]#[N:8])=[CH:3][CH:2]=1.[OH:10]N1C(=O)N(O)C(=O)N(O)C1=O.[C:22]([OH:25])(=[O:24])[CH3:23].O=O>C([O-])(=O)C.[Co+2].C([O-])(=O)C.O>[C:7]([C:4]1[CH:5]=[CH:6][C:23]([C:22]([OH:25])=[O:24])=[CH:2][CH:3]=1)#[N:8].[C:7]([C:4]1[CH:5]=[CH:6][C:1]([CH:9]=[O:10])=[CH:2][CH:3]=1)#[N:8]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 977OxygenHCID 7724p-TolunitrileHCID 104197231,3,5-Trihydroxy-1,3,5-triazinane-2,4,6-trione

Product 2

HCID 120874-Cyanobenzoic acidHCID 660424-Cyanobenzaldehyde

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 962WaterSolvent

Procedure

A mixture of 0.351 g of p-tolunitrile, 0.005 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (1% by mole relative to p-tolunitrile), 5 g of acetic acid and 0.004 g of cobalt(II) acetate.4 H2O was stirred at 100° C. in an atmosphere of oxygene gas (1 atm=0.1 MPa) for 14 hours. The resulting product in the reaction mixture was analyzed by gas chromatography and was found to yield 4-cyanobenzoic acid and 4-cyanobenzaldehyde in 74% and 1% yields, respectively, at 81% conversion of p-tolunitrile.

Sources & evidence

ORD record
ord-9be09ed2220b4b4b810c78380686a65c
Source dataset
uspto-grants-2007_10
Patent number
US07288649B2

Reaction notes

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