Dimethyl Sulfate → Benzoic acid, 2,3,4,5-tetrachloro-6-cyano-, methyl ester

HRID 1111193Notes

Reaction equation

HRID 1111193 reaction equation
[K].[Cl:2][C:3]1[C:4]([C:15]#[N:16])=[C:5]([C:9]([Cl:14])=[C:10]([Cl:13])[C:11]=1[Cl:12])[C:6]([OH:8])=[O:7].S(OC)(O[CH3:21])(=O)=O.[OH-].[K+]>C(C(C)=O)C.O>[Cl:2][C:3]1[C:4]([C:15]#[N:16])=[C:5]([C:9]([Cl:14])=[C:10]([Cl:13])[C:11]=1[Cl:12])[C:6]([O:8][CH3:21])=[O:7]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 5462222PotassiumHCID 140477052,3,4,5-Tetrachloro-6-cyanobenzoic acid

Product 1

HCID 79319Benzoic acid, 2,3,4,5-tetrachloro-6-cyano-, methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A reaction vessel containing 30 ml of water and 60 ml of methyl ethyl ketone is charged with 16.15 g of the dry potassium salt of 3,4,5,6-tetrachloro-2-cyanobenzoic acid. With stirring, the mixture is heated to 72°-74° C. and 9.45 g of dimethyl sulfate are added dropwise at the same temperature to the resultant suspension, while keeping the pH at 6-8 by the gradual addition of 30% potassium hydroxide solution. The reaction mixture is kept under reflux for 2 hours and the aqueous layer is then separated. The organic layer is completely evaporated, affording 12.4 g of methyl 3,4,5,6-tetrachloro-2-cyanobenzoate with a melting point of 82°-83° C.

Workup

  1. temperaturethe mixture is heated to 72°-74° C.
  2. temperatureunder reflux for 2 hours
  3. customthe aqueous layer is then separated
  4. customThe organic layer is completely evaporated

Sources & evidence

ORD record
ord-0902a7edf8ce4560a3dc0065c2dc14cf
Source dataset
uspto-grants-1990_12
Patent number
US04978768

Reaction notes

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