Dimethylformamide → 2-Methoxy-4-methylbenzonitrile

HRID 378325Notes

Reaction equation

HRID 378325 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

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 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. 1H-NMR (DMSO-d6, δ in ppm): 7.60 (d, 1H), 7.05 (s, 1H), 6.90 (d, 1H), 3.90 (s, 3H), 2.40 (s, 3H)

Workup

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

Sources & evidence

ORD record
ord-d3538069fc5f407e8ab1c040ec680ac0
Source dataset
uspto-grants-2000_02
Patent number
US06030972

Reaction notes

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