Methyl iodide → 3-Methoxy-4-methylbenzonitrile

HRID 1584090Notes

Reaction equation

HRID 1584090 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[C:5]#[N:6].[H-].[Na+].[CH3:13]I>CN(C=O)C>[CH3:13][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[C:5]#[N:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 177509203-Hydroxy-4-methylbenzonitrile

Product 1

HCID 147529943-Methoxy-4-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

15 g (0.11 mol) of 3-hydroxy-4-methylbenzonitrile dissolved in 30 ml of DMF were added dropwise to a suspension of 0.11 mol of NaH in 30 ml of DMF, and the mixture was stirred until no further H2 evolution was observed. Then 10.6 ml (0.17 mol) of methyl iodide were added dropwise, and the mixture was stirred at room temperature for 1 h. The solution was poured into ice-water, and the product was extracted with ether/ethyl acetate 7:1. After the solvent had been stripped off, the product began to crystallize slowly. 14.8 g (89%) were obtained. 1H-NMR (CDCl3 ; δ in ppm): 7.2 (m, 2H); 7.02 (s, 1H); 3.85 (s, 3H); 2.25 (s, 3H).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 h
  2. extractionthe product was extracted with ether/ethyl acetate 7:1
  3. customto crystallize slowly
  4. custom14.8 g (89%) were obtained

Sources & evidence

ORD record
ord-cf62a09f7cf24adc8059bc4178b6ee93
Source dataset
uspto-grants-1999_08
Patent number
US05932567

Reaction notes

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