Sulfuric Acid → 3-Methoxy-5-nitrobenzoic acid

HRID 2409445Notes

Reaction equation

HRID 2409445 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+]([O-])=O)[CH:12]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].[CH3:16][O-:17].[Li+].S(=O)(=O)(O)O>CC1CCCC(C)C1=O>[CH3:16][O:17][C:11]1[CH:10]=[C:6]([CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 74333,5-Dinitrobenzoic acidHCID 4177230Lithium methanolate

Product 1

HCID 53002123-Methoxy-5-nitrobenzoic acidYield 70.5%

Reagents, catalysts & solvents 1

HCID 177802,6-DimethylcyclohexanoneSolvent

Procedure

To a stirred solution of 3,5-dinitrobenzoic acid (2.0 g, 9.42 mmol) in 2,6-dimethylcyclohexanone (20.0 ml) was added lithium methoxide (1.43 g, 37.8 mol). The resulting mixture was stirred at room temperature for 20 hours and poured into cold diluted sulfuric acid aqueous solution. The mixture was extracted with diethylether, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain the title compound (1.31 g, yield: 70.25%, reddish brown solid).

Workup

  1. extractionThe mixture was extracted with diethylether
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5994fbc5df3f4d9ba5ca2b41ea392735
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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