Nitric Acid → 1,2,3-Trimethoxy-5-nitrobenzene

HRID 1487214Notes

Reaction equation

HRID 1487214 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([O:18][CH3:19])[C:15]=1[O:16][CH3:17])C(O)=O>C(O)(=O)C>[CH3:19][O:18][C:14]1[CH:13]=[C:9]([N+:1]([O-:4])=[O:2])[CH:8]=[C:7]([O:6][CH3:5])[C:15]=1[O:16][CH3:17]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 83573,4,5-Trimethoxybenzoic Acid

Product 1

HCID 2387701,2,3-Trimethoxy-5-nitrobenzeneYield 66.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of nitric acid (20.0 mL) and acetic acid (40.0 mL) under 10° C. was added 3,4,5-trimethoxybenzoic acid (10.0 g, 47.0 mmol) in portions. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was then poured into ice-water. The resulting precipitate was collected by filtration and washed with water, which was then recrystallized from ethanol to afford the product 1,2,3-trimethoxy-5-nitrobenzene (6.64 g, yield 66.1%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.51 (s, 2H), 3.87 (s, 6H), 3.77 (s, 3H).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with water, which
  3. customwas then recrystallized from ethanol

Sources & evidence

ORD record
ord-0a50e49e80814aef8dd305d7453b830f
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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