Dimethyl Sulfate → Methyl 3-chloro-5-cyano-4-methoxybenzoate

HRID 385023Notes

Reaction equation

HRID 385023 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:13]#[N:14])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[C:15](=O)([O-])[O-].[K+].[K+].COS(=O)(=O)OC>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:13]#[N:14])[C:11]=1[O:12][CH3:15])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 68108871Methyl 3-chloro-5-cyano-4-hydroxybenzoate

Product 1

HCID 68108614Methyl 3-chloro-5-cyano-4-methoxybenzoateYield 76.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-chloro-5-cyano-4-hydroxybenzoate (1.27 g) was dissolved in N,N-dimethylformamide (20 mL), and potassium carbonate (5.00 g) and dimethylsulfuric acid (1.70 mL) were added to the solution, and then the mixture was stirred at room temperature for 18 hours. The reaction solution was filtered and water was added, and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (1.03 g) as a colorless crystal.

Workup

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

Sources & evidence

ORD record
ord-103dc149019a491782a97364fb3dd1fd
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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