Nitric Acid → (4,5-Dimethoxy-2-nitro-phenyl)-acetic acid

HRID 1589822Notes

Reaction equation

HRID 1589822 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N+:15]([O-])([OH:17])=[O:16]>CCOCC.C(O)(=O)C>[CH3:10][O:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([CH2:11][C:12]([OH:14])=[O:13])=[C:6]([N+:15]([O-:17])=[O:16])[CH:7]=1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 7139(3,4-Dimethoxyphenyl)acetic acid

Product 1

HCID 270941(4,5-Dimethoxy-2-nitro-phenyl)-acetic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

3,4-Dimethoxyphenylacetic acid (7.84 g) was solubilised in ether (100 ml) and acetic acid (20 ml). Fuming nitric acid (1.68 ml) was added dropwise to the solution. Stirring was maintained at room temperature for 16 hours. The precipitate was collected by filtration, washed with ether and dried to give 4,5-dimethoxy-2-nitrophenylacetic acid (4.19 g); NMR (DMSO-d6) 3.88(s,3H); 3.80(s,3H); 3.97(s,2H); 7.15(s,1H); 7.70(s,1H).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with ether
  3. customdried

Sources & evidence

ORD record
ord-9f83b425a0784eaf9ca43726eff541fa
Source dataset
uspto-grants-1993_04
Patent number
US05200404

Reaction notes

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