Nitric Acid → 3-Methanesulfonyl-5-nitrobenzoic acid

HRID 1373102Notes

Reaction equation

HRID 1373102 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[N+:14]([O-])([OH:16])=[O:15].C(=O)(O)[O-].[Na+]>OS(O)(=O)=O.O=S(=O)=O>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 2203803-Methanesulfonylbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 223974393-Methanesulfonyl-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 24681Fuming sulfuric acidSolvent

Procedure

A solution of 3-methylsulfonylbenzoic acid (16.3 g) in 20% oleum (100 ml) was cooled (ice-bath) and fuming nitric acid (>90%; 90 ml) was added dropwise. The resulting mixture was stirred for 4 days at room temperature and was then poured onto crushed ice. The acids were partially neutralised by addition of solid sodium bicarbonate (to ˜pH2). The solid precipitate was filtered off and dried to give, as a pale beige solid D11 (15.6 g).

Workup

  1. additionwas added dropwise
  2. additionwas then poured
  3. customonto crushed ice
  4. filtrationThe solid precipitate was filtered off
  5. customdried
  6. customto give, as a pale beige solid D11 (15.6 g)

Sources & evidence

ORD record
ord-6b5fef9245334028b30946959d4cd2a3
Source dataset
uspto-grants-2007_01
Patent number
US07160905B2

Reaction notes

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