Sulfuric Acid → 4-Chloro-2-nitroanisole

HRID 2417345

Reaction equation

HRID 2417345 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:11])([O-:3])=[O:2].[Cl-:12].[Na+].S(=O)(=O)(O)O.I([O-])(=O)(=O)=O.[Na+]>C(#N)C.O>[N+:1]([C:4]1[CH:9]=[C:8]([Cl:12])[CH:7]=[CH:6][C:5]=1[O:10][CH3:11])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 70482-NitroanisoleHCID 23667635Sodium periodate

Product 1

HCID 666314-Chloro-2-nitroanisole

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

2-Nitroanisole (1 mmol) was treated with sodium chloride (1.2 mmol) in acetonitrile: water (2:1, 6 ml). 20% Sulfuric acid (5 ml) and sodium periodate (20 mol %) was added to the reaction mixture. The mixture was heated at 80° C. under inert atmosphere for 4 h. The product was purified by column chromatography to give 2-nitro-4-chloroanosole (55%).

Workup

  1. customThe product was purified by column chromatography
  2. customto give 2-nitro-4-chloroanosole (55%)

Sources & evidence

ORD record
ord-9c6fe26de6574594bc79c77b3f5f7741
Source dataset
uspto-grants-2004_11
Patent number
US06825383B1

Linked notes

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