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

HRID 1606614Notes

Reaction equation

HRID 1606614 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][S:6]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[Cl:18])[C:12]([OH:14])=[O:13])(=[O:8])=[O:7]>S(=O)(=O)(O)O>[CH3:5][S:6]([C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([N+:1]([O-:4])=[O:2])[C:17]=1[Cl:18])[C:12]([OH:14])=[O:13])(=[O:8])=[O:7]

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×

Conditions

Temperature
15 °C

Procedure

To a stirred mixture of concentrated sulfuric acid (75 ml.) and concentrated nitric acid (48 ml.), cooled to 15° C., is added a solution of 3-methylsulfonyl-4-chlorobenzoic acid (31.5 g.; 0.134 mole) in concentrated sulfuric acid (185 ml.). The reaction mixture is heated on a steam bath for 21/2 hours then poured into ice. There is collected 34 g. (91%) of 3-methylsulfonyl-4-chloro-5-nitrobenzoic acid, m.p. 197° C. after recrystallization from ethanol.

Workup

  1. temperatureThe reaction mixture is heated on a steam bath for 21/2 hours
  2. additionthen poured into ice
  3. customThere is collected 34 g
  4. custom(91%) of 3-methylsulfonyl-4-chloro-5-nitrobenzoic acid, m.p. 197° C. after recrystallization from ethanol

Sources & evidence

ORD record
ord-9535328963e74981b3bcdcc1602f8660
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

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