4-Methylbenzaldehyde → p-Tolunitrile

HRID 1885067Notes

Reaction equation

HRID 1885067 reaction equation
N(OC(C)(C)C)=O.ON1C(=O)C2=CC=CC=C2C1=O.[CH3:20][C:21]1[CH:29]=[CH:28][C:24]([CH:25]=[N:26]O)=[CH:23][CH:22]=1.CC1C=CC(C=O)=CC=1>C(O)(=O)C.CC1C=CC(C)=CC=1>[CH3:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 77254-MethylbenzaldehydeHCID 10665N-HydroxyphthalimideHCID 10906Tert-Butyl nitriteHCID 19475HCID 19475, compound

Product 1

HCID 7724p-Tolunitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7809P-XyleneSolvent

Conditions

Temperature
60 °C

Procedure

In a flask p-xylene (1 ml), t-butyl nitrite (1 mmol), N-hydroxyphthalimide (0.1 mmol), and acetic acid (1 ml) were placed and were stirred at 60° C. in an atmosphere of argon gas (1 atm=0.101 MPa) for 20 hours. The resulting reaction mixture was analyzed to find that p-methylbenzaldehyde oxime, p-methylbenzaldehyde, and p-methylbenzonitrile were formed in yields of 60%, 3%, and 3%, respectively.

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-3f35aacc79594bd4ad9947a6675801eb
Source dataset
uspto-grants-2004_07
Patent number
US06768023B2

Reaction notes

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