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

HRID 1854142Notes

Reaction equation

HRID 1854142 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].OS(O)(=O)=O.[N+:17]([O-])([OH:19])=[O:18]>>[Cl:1][C:2]1[CH:3]=[C:4]([N+:17]([O-:19])=[O:18])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 820095-Chloro-2-methylbenzoic acid

Product 1

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

Procedure

A stirred solution of 5-chloro-2-methylbenzoic acid (1 mmol) in cone. 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-7d7fbb44ce054987b2d3e960d9c802d7
Source dataset
uspto-grants-2015_02
Patent number
US08962620B2

Reaction notes

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