Methyl iodide → Methyl 4-cyano-3-methoxybenzoate

HRID 1871192Notes

Reaction equation

HRID 1871192 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[OH:15])#[N:4].IC.[CH3:18]COC(C)=O.O>CN(C=O)C>[C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[O:15][CH3:18])#[N:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 16641129Methyl 4-cyano-3-hydroxybenzoateHCID 22728543Water ethylacetate

Product 1

HCID 22464400Methyl 4-cyano-3-methoxybenzoateYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (9 g, 0.24 mol as 60% wt. disp. mineral oil) was added to a solution of the phenol from Step C (36.1 g, 204 mmol) in 400 mL of dry DMF at room temperature. Iodomethane was added (14 mL. 0.22 mol) was added, and the reaction was stirred for 2 hours. The mixture was poured into EtOAc/water, and the organic layer was washed with water and brine (4x), dried (Na2SO4), and concentrated in vacuo to provide the titled product (37.6 g, 96% yield).

Workup

  1. additionwas added
  2. washthe organic layer was washed with water and brine (4x)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8c9b732d00749809f697c1062f90167
Source dataset
uspto-grants-2000_08
Patent number
US06103487

Reaction notes

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