Nitric Acid → HCID 21699291, compound

HRID 634664Notes

Reaction equation

HRID 634664 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][O:17][CH3:18])[C:6]([O:8][CH2:9][CH3:10])=[O:7].[N+:19]([O-])([OH:21])=[O:20]>O>[CH3:1][O:2][C:3]1[C:13]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:12][C:11]([N+:19]([O-:21])=[O:20])=[C:5]([CH:4]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 22467437HCID 22467437, compound

Product 1

HCID 21699291HCID 21699291, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 3-methoxy-4-(2-methoxyethoxy)benzoate (9.5 g, 37 mmol) was added portionwise to stirred concentrated nitric acid (75 ml) at 0° C. The mixture was allowed to warm to ambient temperature and stirred for a further 90 minutes. The mixture was diluted with water and extracted with methylene chloride, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with hexane to give ethyl 5-methoxy-4-(2-methoxyethoxy)-2-nitrobenzoate (10.6 g, 95%) as an orange solid.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed by evaporation
  4. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-45a93cf69f504c26a1040e29ec7112fc
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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