Nitric Acid → 1,2-Dichloro-4-methyl-5-nitrobenzene

HRID 842926

Reaction equation

HRID 842926 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[N+:10]([O-])([OH:12])=[O:11]>O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[C:4]([CH3:9])[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 7256Benzene, 1,2-dichloro-4-methyl-

Product 1

HCID 3437951,2-Dichloro-4-methyl-5-nitrobenzeneYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To stirred 3,4-dichloro-toluene 4 (10.0 g, 62.2 mmol) at 0° C. was slowly added fuming nitric acid (20.0 mL). The mixture was stirred for 2 hrs at RT, then water added (200 mL) and the reaction mixture filtered. The filtrate was purified by silica gel chromatography using 5% ethyl acetate in hexanes to give the title compound 11.7 g (92%). 1H NMR (400 MHz, CDCl3) δ8.14 (s, 1 H, Ar), 7.47 (s , 1 H, Ar), 2.59 (s, 3 H, CH3).

Workup

  1. filtrationthe reaction mixture filtered
  2. customThe filtrate was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a02dd13d827044d48b0a3fc2d4c19342
Source dataset
uspto-grants-2002_04
Patent number
US06376530B1

Linked notes

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