Nitric Acid → 3-Methylsulfonyl-4-chloro-5-nitrobenzoic acid

HRID 399788Notes

Reaction equation

HRID 399788 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[S:15]([CH3:18])(=[O:17])=[O:16]>S(=O)(=O)(O)O>[Cl:5][C:6]1[C:14]([N+:1]([O-:4])=[O:2])=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[S:15]([CH3:18])(=[O:16])=[O:17]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1826704-Chloro-3-methanesulfonylbenzoic acid

Product 1

HCID 122745753-Methylsulfonyl-4-chloro-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To the mixture of conc. sulfuric acid (53.3 ml) and conc. nitric acid (36.0 ml) was added dropwise a solution of 4-chloro-3-methylsulfonylbenzoic acid (22.5 g) in conc. sulfuric acid (135.0 ml) for 10 minutes at 20°-30° C., and the mixture was stirred for 5 hours at 75°-80° C. After ice-cooling, the mixture was poured into ice-water and isolated precipitate was collected by filtration to give 4-chloro-3-methylsulfonyl-5-nitrobenzoic acid (24.85 g).

Workup

  1. temperatureAfter ice-cooling
  2. customisolated precipitate
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-6185fcf560704808b789b3b32865d9e9
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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