Dimethyl Sulfate → HCID 33779672, compound

HRID 385089Notes

Reaction equation

HRID 385089 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([I:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[C:14](=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]([I:13])[C:11]=1[O:12][CH3:14])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 68108695HCID 68108695, compound

Product 1

HCID 33779672HCID 33779672, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-chloro-4-hydroxy-5-iodobenzoate (3.00 g) was dissolved in N,N-dimethylformamide (20 mL), and potassium carbonate (3.98 g) and dimethylsulfuric acid (1.82 mL) were added to the solution, and then the mixture was stirred at room temperature for 5 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 (2.96 g) as a pale yellow 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-915f539c9d9b4dfd80fc1578a2a3b07c
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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