Dimethylformamide → 2-Methoxy-4-methylbenzonitrile

HRID 2184241Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4](O)[C:5](=C[CH:9]=1)C=O.[CH3:11]I.[C:13]([O-:16])([O-])=O.[K+].[K+].C[N:20]([CH:22]=O)C>>[CH3:11][O:16][C:13]1[CH:1]=[C:2]([CH3:9])[CH:3]=[CH:4][C:5]=1[C:22]#[N:20]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6328Methyl iodide

HCID 11430Potassium Carbonate

HCID 612002-Hydroxy-4-methylbenzaldehyde

Product 1

HCID 124953732-Methoxy-4-methylbenzonitrile

Procedure

10.7 g (78.6 mmol) of 4-methylsalicylaldehyde (J. C. S. Perkin I (1980) 1862) were methylated with 5.8 ml of MeI in the presence of 13 g of K2CO3 in 40 ml of DMF. The reaction mixture was poured into ice-water, and the product (11.5 g) was extracted with ether. The aldehyde was converted into the nitrile by a method similar to that in Synthesis (1978) 11.

Workup

extractionthe product (11.5 g) was extracted with ether
customin Synthesis (1978) 11

Sources & evidence

ORD record: ord-3544d2d081124f3c8bfb8225f48a29e5
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900319B2

Reaction notes

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