Nitrogen → 2-Hydroxy-5-(methoxycarbonyl)benzoic acid

HRID 444988Notes

Reaction equation

HRID 444988 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:6]([C:7]([O:9]C)=[O:8])[CH:5]=1.N#N.CCCCCCC.CCOC(C)=O.CC(O)=O>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 80087Dimethyl 4-hydroxyisophthalateHCID 86619247EtOAc heptane acetic acid

Product 1

HCID 127170602-Hydroxy-5-(methoxycarbonyl)benzoic acidYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The compound was prepared in the manner described by Coutts, Ian G. C.; Edwards, Mark; Richards, David J. Synthesis 1981, 487. 4-Hydroxy isophthalic acid dimethyl ester (5.28 g, 25.1 mmol) was refluxed in pyridine under a flow of N2. The reaction was monitored via TLC (20:10:1, heptane/AcOEt/AcOH) which indicated reaction completion after 8 h. The majority of the pyridine was removed under vacuum, and AcOEt (100 ml) was added. The solution was washed with 0.5 M HCl (3×50 ml). The acidic washes were then extracted with AcOEt (100 ml). The two organic phases were pooled, dried (MgSO4) and concentrated to yield a white solid (4.85 g, 99%). The solid was recrystallized from toluene (200 ml) to yield white crystals (4.6 g, 92%).

Workup

  1. customThe compound was prepared in the manner
  2. customSynthesis 1981, 487
  3. customreaction completion after 8 h
  4. customThe majority of the pyridine was removed under vacuum, and AcOEt (100 ml)
  5. additionwas added
  6. washThe solution was washed with 0.5 M HCl (3×50 ml)
  7. extractionThe acidic washes were then extracted with AcOEt (100 ml)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a7273e53ee454058a8d26515ae16e5a7
Source dataset
uspto-grants-2013_07
Patent number
US08476228B2

Reaction notes

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