p-Toluenesulfonic acid monohydrate → Methyl 2-ethoxy-4-nitrobenzoate

HRID 1807271

Reaction equation

HRID 1807271 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].O.[C:17]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH3:17])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 27363472-Ethoxy-4-nitrobenzoic acid

Product 1

HCID 9964566Methyl 2-ethoxy-4-nitrobenzoateYield 311%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-ethoxy-4-nitrobenzoic acid (2.035 g, 9.45 mmol, Aldrich) in methanol (40 ml) was treated with p-toluenesulfonic acid monohydrate (583.3 mg, 3.07 mmol) and heated at reflux under argon for 17 hrs. The solvent was removed and the residue was dissolved in ethyl acetate, washed with saturated Na2CO3, water and saturated NaCl and dried over Na2SO4, filtered and concentrated to give methyl 2-ethoxy-4-nitrobenzoate (2.15 g, 101%) as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux under argon for 17 hrs
  3. customThe solvent was removed
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with saturated Na2CO3, water and saturated NaCl
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d238a603e8ad424fabe4acc8048d82ce
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Linked notes

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