Dimethyl Sulfate → 4-Chloro-2-nitroanisole

HRID 2057570

Reaction equation

HRID 2057570 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:12])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 69804-Chloro-2-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 666314-Chloro-2-nitroanisole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.072 mol (12.6 g) of 4-chloro-2-nitrophenol, 40 ml of acetone and 9.72 g of potassium carbonate are introduced into a 250 ml three-necked flask equipped with a stirring system, a thermometer and a condenser. The mixture is brought to 40° C. and 9.72 g of dimethyl sulphate are then added drop by drop; the mixture is heated under reflux for 5 hours; the potassium sulphate is separated; the acetone solution is concentrated under reduced pressure and the 4-chloro-2-nitroanisole is precipitated. It is separated and then crystallized in a water/acetone mixture.

Workup

  1. customequipped with a stirring system
  2. customis brought to 40° C.
  3. temperaturethe mixture is heated
  4. temperatureunder reflux for 5 hours
  5. customthe potassium sulphate is separated
  6. concentrationthe acetone solution is concentrated under reduced pressure
  7. customthe 4-chloro-2-nitroanisole is precipitated
  8. customIt is separated
  9. customcrystallized in a water/acetone mixture

Sources & evidence

ORD record
ord-84f8493b1e3d454485e7ff009f8de7aa
Source dataset
uspto-grants-1980_07
Patent number
US04211776

Linked notes

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