Nitric Acid → 2-Nitro-4-chloro-6-methylanisole

HRID 1166227Notes

Reaction equation

HRID 1166227 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH3:10])[CH:3]=1.[N+:11]([O-])([OH:13])=[O:12].OS(O)(=O)=O>>[N+:11]([C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]([CH3:10])[C:5]=1[O:8][CH3:9])([O-:13])=[O:12]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 767484-Chloro-2-methylanisole

Product 1

HCID 229976382-Nitro-4-chloro-6-methylanisoleYield 41%

Procedure

4-Chloro-2-methylanisole (46.8 g) was added dropwise to a mixture of concentrated HNO3 (33 ml) and H2SO4 (99 ml) at 0° C. The reaction mixture was then poured into a ice water and extracted with dichloromethane. The organic layer was washed with water, dried over MgSO4, and concentrated in vacuo to give a residue. The residue was purified by flash chromatography over silica gel (elution with 5% ethyl acetate in hexanes) to give 25 g (41%) of 2-nitro-4-chloro-6-methylanisole. 1H NMR (300 MHz, CDCl3) δ7.64 (d, J=2.5 Hz, 1 H), 7.40 (d, J=2.5 Hz, 1 H), 3.89 (s, 3 H), 2.36 (s, 3 H).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give a residue
  6. customThe residue was purified by flash chromatography over silica gel (elution with 5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-41140dc133f44d67b199fe6679fc392e
Source dataset
uspto-grants-2003_09
Patent number
US06613786B2

Reaction notes

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