Nitric Acid → 4-Nitro-1,2-benzenediacetic acid

HRID 488380Notes

Reaction equation

HRID 488380 reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([OH:10])=[O:9].[N+:15]([O-])([OH:17])=[O:16]>S(=O)(=O)(O)O>[N+:15]([C:5]1[CH:6]=[C:1]([CH2:11][C:12]([OH:14])=[O:13])[C:2]([CH2:7][C:8]([OH:10])=[O:9])=[CH:3][CH:4]=1)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 24123o-Phenylenediacetic acid

Product 1

HCID 222696224-Nitro-1,2-benzenediacetic acidYield 65%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a stirred solution of 1,2-phenylenediacetic acid (10.2 g, 52.5 mmol) in conc. sulfuric acid (33 mL), cooled to −10° C., is added over 10 min a mixture of nitric acid (3.9 mL) and sulfuric acid (1.3 mL). After stirring at −10° C. for 4 h, the reaction mixture is poured onto ice (250 cc). The resulting mixture is extracted with ethyl acetate (3×300 mL). The combined organic phases are washed with H2O (100 mL), dried (MgSO4), filtered and concentrated to afford a white solid. The solid is recrystallized from methyl-tert-butyl ether in hexane to give 8.2 g (34.3 mmol, 65%) of the desired product. mp 187-188° C.

Workup

  1. additionis added over 10 min
  2. additionthe reaction mixture is poured onto ice (250 cc)
  3. extractionThe resulting mixture is extracted with ethyl acetate (3×300 mL)
  4. washThe combined organic phases are washed with H2O (100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a white solid
  9. customThe solid is recrystallized from methyl-tert-butyl ether in hexane

Sources & evidence

ORD record
ord-5e40fd121fde4114a17f54197768bcfe
Source dataset
uspto-grants-2005_12
Patent number
US06972286B2

Reaction notes

Loading…