Nitric Acid → Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate

HRID 2189240Notes

Reaction equation

HRID 2189240 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH2:19][O:20][CH3:21])[C:9]([O:11][CH2:12][CH3:13])=[O:10].[N+:22]([O-])([OH:24])=[O:23].O>C(O)(=O)C>[CH3:21][O:20][CH2:19][CH2:18][O:17][C:16]1[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:14]([N+:22]([O-:24])=[O:23])[CH:15]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 2808992Ethyl 3,4-bis(2-methoxyethoxy)benzoate

Product 1

HCID 11186961Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoateYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of ethyl 3,4-bis(2-methoxyethoxy)benzoate (23.23 g, 77.87 mmol) in acetic acid (80 mL) was added dropwise to concentrated nitric acid (21 mL) cooled with an ice bath at such a rate as to keep the internal temperature below 5° C. After 30 min, the solution was allowed to warm to room temperature and stirred for 48 h. The solution was poured onto iced water (400 mL) and extracted with ethyl acetate (3×100 mL). The organic phases were combined and washed cautiously with saturated aqueous sodium bicarbonate (3×200 mL) and brine (2×100 mL). The organic phase was dried (Na2SO4) and concentrated to give the title compound as a solid (24.82 g, 93%).

Workup

  1. temperaturecooled with an ice bath at such a rate as
  2. customthe internal temperature below 5° C
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washwashed cautiously with saturated aqueous sodium bicarbonate (3×200 mL) and brine (2×100 mL)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4322c739e9544631952e793a720c445e
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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