Nitric Acid → 4-Chloro-5-chlorosulfonyl-3-nitrobenzoic acid

HRID 1606619Notes

Reaction equation

HRID 1606619 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[Cl:10][S:11]([C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[Cl:23])[C:17]([OH:19])=[O:18])(=[O:13])=[O:12]>>[N+:6]([C:21]1[CH:20]=[C:16]([CH:15]=[C:14]([S:11]([Cl:10])(=[O:13])=[O:12])[C:22]=1[Cl:23])[C:17]([OH:19])=[O:18])([O-:9])=[O:7]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 756134-Chloro-3-(chlorosulphonyl)benzoic acid

Product 1

HCID 898924-Chloro-5-chlorosulfonyl-3-nitrobenzoic acid

Procedure

To a mixture of concentrated sulfuric acid (87 ml.) and concentrated nitric acid (16 ml., density = 1.42) is added 3-chlorosulfonyl-4-chlorobenzoic acid (11.5 g.; 0.045 mole). The reaction mixture is heated at 85°-90° C. with stirring for 20 hours then poured into ice water. The 3-nitro-4-chloro-5-chlorosulfonylbenzoic acid which separates is filtered, washed with water and dried, m.p. = 189°-90° C. (corr.); yield, 6.6 g. (50%).

Workup

  1. temperatureThe reaction mixture is heated at 85°-90° C.
  2. filtrationThe 3-nitro-4-chloro-5-chlorosulfonylbenzoic acid which separates is filtered
  3. washwashed with water
  4. customdried
  5. customyield

Sources & evidence

ORD record
ord-5eccbb2fea6045a29bfb2ed328fcf58a
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

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