Sulfuric Acid → 3-Chlorobenzoic Acid

HRID 426927Notes

Reaction equation

HRID 426927 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5](N)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.C(O)(C)C.N([O-])=O.[Na+]>O>[Cl:1][C:2]1[CH:10]=[C:6]([CH:5]=[CH:4][CH:3]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 124762-Amino-5-chlorobenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 4473-Chlorobenzoic AcidYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

172 parts of 5-chloroanthranilic acid are introduced into 550 parts of 45 percent strength by weight sulfuric acid and 600 parts of isopropanol. A solution of 100 parts of sodium nitrite in 140 parts of water is run in at 80° C. over 6 hours; nitrogen is evolved. The mixture is cooled, 1,500 parts of water are added and the product is filtered off. 140 parts (89% of theory) of 3-chlorobenzoic acid of melting point 151°-153° C. are obtained.

Workup

  1. temperatureThe mixture is cooled
  2. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-2e39d1deaec94a0cba9b4863c0cd3dcd
Source dataset
uspto-grants-1979_10
Patent number
US04172098

Reaction notes

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