Dimethyl Sulfate → Methyl 3-cyano-4-methoxybenzoate

HRID 385132Notes

Reaction equation

HRID 385132 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])#[N:2].[C:14](=O)([O-])[O-].[K+].[K+].COS(=O)(=O)OC>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 11769089Methyl 3-cyano-4-hydroxybenzoate

Product 1

HCID 2801011Methyl 3-cyano-4-methoxybenzoateYield 85.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-cyano-4-hydroxybenzoate (1.00 g) was dissolved in N,N-dimethylformamide (5 mL), and potassium carbonate (1.56 g) and dimethylsulfuric acid (0.70 mL) were added to the solution, and then the mixture was stirred at room temperature for 1 hour. After the reaction solution was filtered, water was added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (923 mg) as a yellow solid.

Workup

  1. filtrationAfter the reaction solution was filtered
  2. additionwater was added
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-820de3d242ab4ede8d5eea0516ab8c9e
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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