Sulfuric Acid → 3,5-Dichlorobenzoic acid

HRID 426924Notes

Reaction equation

HRID 426924 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1N.S(=O)(=O)(O)O.C(O)(C)C.N([O-])=O.[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 760363,5-Dichloroanthranilic acidHCID 23668193Sodium Nitrite

Product 1

HCID 58113,5-Dichlorobenzoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

206 parts of 3,5-dichloroanthranilic acid are introduced into 500 parts of 45 percent strength by weight sulfuric acid and 400 parts of isopropanol. A solution of 100 parts of sodium nitrite in 140 parts of water is run in over 5 hours at 80° C.; nitrogen is evolved. The mixture is cooled, 1,000 parts of water are added and the product is filtered off. 172 parts (90% of theory) of 3,5-dichlorobenzoic acid of melting point 175°-178° C. are obtained.

Workup

  1. customis run in over 5 hours at 80° C.
  2. temperatureThe mixture is cooled
  3. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-b12ef2e6b0e54d26b4b93647e3c52208
Source dataset
uspto-grants-1979_10
Patent number
US04172098

Reaction notes

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