Dimethyl Sulfate → 4-Methoxy-3-nitrobenzonitrile

HRID 2185925Notes

Reaction equation

HRID 2185925 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>C(#N)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH3:13])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1)#[N:7]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 767584-Hydroxy-3-nitrobenzonitrile

Product 1

HCID 28002414-Methoxy-3-nitrobenzonitrileYield 98.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 8.37 g of 4-hydroxy-3-nitrobenzonitrile, 27.64 g of anhydrous potassium carbonate and 6 mL of dimethyl sulphate in 60 mL of acetonitrile was stirred at reflux for 2 hours. The solvent was removed by evaporation in vacuo. The residue was taken up in 100 mL of water and extracted with 3×80 mL of chloroform. The combined organic layers were dried over sodium sulphate and the solvent was evaporated off to afford 8.8 g (98.8%) of Compound 18A as an ivory solid.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe solvent was removed by evaporation in vacuo
  3. extractionextracted with 3×80 mL of chloroform
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-975a75e2bdec46bf9d67975710e0b832
Source dataset
uspto-grants-2002_06
Patent number
US06403594B1

Reaction notes

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