Nitric Acid → 5-Chloro-2-methyl-3-nitrobenzoic acid

HRID 1501695Notes

Reaction equation

HRID 1501695 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 820095-Chloro-2-methylbenzoic acid

Product 1

HCID 230097625-Chloro-2-methyl-3-nitrobenzoic acidYield 60%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A stirred solution of 5-chloro-2-methylbenzoic acid (1 mmol) in conc. H2SO4 (2 mL) was cooled to −10° C. and nitrating mixture (0.4 mL of conc. H2SO4+0.1 mL of conc. HNO3) was added to it in dropwise manner. The reaction mixture was stirred at the same temperature for 20 min then warmed to room temperature. The solid precipitate was filtered and dried to obtain 5-chloro-2-methyl-3-nitrobenzoic acid which was used in next step without further purification (yield 60-70%).

Workup

  1. filtrationThe solid precipitate was filtered
  2. customdried

Sources & evidence

ORD record
ord-bfab7be9238c446b8970d45b2006cf49
Source dataset
uspto-grants-2015_12
Patent number
US09206157B2

Reaction notes

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