Methyl iodide → 3-Methoxy-4-methylbenzonitrile

HRID 2184232Notes

Reaction equation

HRID 2184232 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-methylbenzonitrileYield 91.4%

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 and 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 RT 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 slowly to crystallize. 14.8 g (89%) of the product 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 RT for 1 h
  2. extractionthe product was extracted with ether/ethyl acetate 7:1
  3. customto crystallize

Sources & evidence

ORD record
ord-06fd7d6074b24f19820145fcf8d1b0ac
Source dataset
uspto-grants-2005_05
Patent number
US06900319B2

Reaction notes

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