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

HRID 1111192Notes

Reaction equation

HRID 1111192 reaction equation
[Na].[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-].[Na+]>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 14798Sodium HydroxideHCID 5360545SodiumHCID 140477052,3,4,5-Tetrachloro-6-cyanobenzoic acid

Product 1

HCID 79319Benzoic acid, 2,3,4,5-tetrachloro-6-cyano-, methyl esterYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A reaction vessel is charged in succession with 360 g of water, 475 g of methyl ethyl ketone and 307 g (1.0 mole) of the sodium salt (dry) of 3,4,5,6-tetrachloro-2-cyanobenzoic acid. With stirring, the mixture is heated to 72°-74° C. and to the suspension so obtained are added, at this temperature and over 1 hour, 189 g of dimethyl sulfate (1.5 moles), while keeping the pH at 5.0-5.5 by the gradual addition of 66 g (0.5 mole) of 30% sodium hydroxide solution. The reaction mixture is then stirred for 1 hour at reflux temperature (72°-74° C.). Conventional working up affords a yield of 93% of theory of methyl 3,4,5,6-tetrachloro-2-cyanobenzoate, based on the sodium salt of 3,4,5,6-tetrachloro-2-cyanobenzoic acid.

Workup

  1. temperaturethe mixture is heated to 72°-74° C. and to the suspension
  2. customso obtained
  3. additionare added, at this temperature and over 1 hour
  4. stirringThe reaction mixture is then stirred for 1 hour
  5. temperatureat reflux temperature (72°-74° C.)

Sources & evidence

ORD record
ord-63bebe2aff824f09b1a73aa4b320b1b1
Source dataset
uspto-grants-1990_12
Patent number
US04978768

Reaction notes

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